All depends how much confidence I still have in the project really. If I still think it has the potential to succeed, then it could be worth investing some more and bringing down my average buying price, that would give me a lower break even point. If I've lost confidence, then probably best to cut my losses and look elsewhere. Personally I have done both, it's a tough decision to make when you cash in a loss, but worth it if you believe it will perform better in another investment.

Was having this conversation with a friend tonight, 'the perfect time to buy'. I think what we ended up with was that there are loads of different 'perfect times' to buy. Back in September seemed like a great time to us, now is a great time for anyone new, in another few months we'll probably be looking at another 'perfect time'. Who knows, get involved and take it from there.

Using this Cost of Living website, here's what you could have bought with $100 back in 2010.

40 loaves of Sara Lee White Bread (enough for more than 600 slices of toast)
or
192 lbs of Russet potatoes (approximately 580 large portions of fries from McDonalds)
or
35 gallons of milk from Prairie Farms (Ben & Jerry's could rustle up 3 gallons of ice cream for you)
or
31 lbs of Hormel bacon (over 600 generous thick cut bacon sandwiches if you wanted to use some of that Sara Lee bread)
or
73 dozen eggs (that's one boiled egg a day for 876 days)
or
343 cans of Coke (3773 grams of sugar would be enough for 150 days of the recommended daily limit for women, or 100 days for men)
or
100 Scott toilet rolls (depending on your dietary habits, these should keep your bathroom visits sorted for over a year)
or
48 tins of Campbells Cream of Chicken Soup (these'll get you through a winter season's worth of cold weather)
or
33 large boxes of Kellogg's Cornflakes (that's a bowl of Cornflakes every day for 594 days)
or
34 Jack's Pepperoni Pizzas (that's Monday Night Football snacks sorted for a few months)
or
26 lbs of Ground Beef (invite the neighbours over and get the BBQ going for the 83 burgers you're going to be cooking)
or
36 Gallons of Gas (that would get your Mini Cooper from Vancouver down to Tijuana for an epic road trip - don't forget your passport)

And just for sh*ts and giggles, 2010 was the year of the Bitcoin pizza, when Laszlo Hanyecz bought two pizzas in Jacksonville, Florida for 10,000 Bitcoin on 22nd May.

If you had decided to buy Bitcoin with your $100, you would have been able to buy around 25,000 of them, worth almost $187 million today.

Is there any real benefit to a company running an ICO that lasts a long time to attract more investors, or is it best to get it over quickly so that people are encouraged to rush to invest?

If the length of the ICO is stated clearly at the beginning, then personally I don't think that there is any real difference. The issue comes, both for investors and bounty hunters, when the dates get extended/changed during the ICO. This is rarely a good sign, as it most likely means that they are not raising as much funds as they anticipated (whatever the excuse/reason that the ICO manager themselves give). It can be for genuine reasons though, so it does not necessarily mean you have picked a three legged horse.

It is frustrating as an investor when you have invested early because of the bonuses on offer, and then the same (or even better bonuses) are offered during the latter stages. Unfortunately there is nothing you can do, and the bottom line is that you want the project to be successful, otherwise your investment is likely to lose some/all of it's value anyway. I would rather a project extended it's ICO and managed to hit their targets, than finish on time and struggle to deliver on their vision. Some of the best cryptocurrencies started off as slow burners, so a drawn out, support lacking ICO is not necessarily a bad thing, but it does imply that you are probably best waiting until it hits the exchanges as demand is still likely to be low.

I was recently reading an article about the best countries to set up ICOs. Makes for some interesting reading, with the majority of the Top 10 (at least according to this article) being in Europe. A surprising country, in my opinion anyway, was the UAE. I didn't expect any country in the Middle East to feature, but apparently they 'plan on being the world's first blockchain powered government'. Whether this actually turns out to be true is another matter, but they definitely seem more open to the blockchain evolution than other (theoretically) more open countries. Here's a link to the article anyway.

https://behaviour.exchange/10-world-countries-vibrant-ico-scene/

With regulations constantly changing, I wouldn't be surprised to see a completely different list in a year's time.

Anyone in this forum has (probably) already weighed up the risks of investing in Bitcoin, but 'we' are still just a drop in the ocean compared to the number of potential investors, my dad included. So what is putting him off investing? Here are a few of the reasons investors are either delaying their involvement or (and this - regrettably - applies to many of my friends and family, although I am winning some of them around slowly!) currently have the opinion that they wouldn't touch it with a ten foot barge pole.

1. Media FUD - they only read headlines, and with the number of negative articles about Bitcoin compared to the positive ones, they're being scared away without bothering to look at the whole picture. This article is just one of a flood of negative articles about cryptocurrency.

https://www.theguardian.com/technology/2018/jan/15/should-i-invest-bitcoin-dont-mr-money-moustache

Until the media changes it's stance on cryptocurrency, they will still be able to steer millions of potential investors away. Only a matter of time.

2. Market Volatility - traditional investors tend to veer to towards steady investments, a yearly return of between 10-20% is a healthy addition to a pension fund without risking losing the lot, especially for those looking to retire in the next 10-15 years. A cryptocurrency investor (at least in the current market) is much more of a risk taker, willing to take a gamble on new technology. The following article states that the volatility is a result of liquidity (specifically lack of), an argument that probably holds a decent amount of water. This is especially paramount for the institutional investors to get involved, but has a knock on effect for the average investor. 

https://www.cnbc.com/2017/09/21/bitcoin-volatility-how-digital-currency-can-overcome-wild-reputation.html

3. Fear of legislation (this factor can vary depending on location) and government's knee jerk reaction to cryptocurrency. A majority of people, unfortunately, still blindly trust their government, even though this is proving to be an unwise tactic, proven by the growing number of scandals exposed as the internet removes previous impenetrable  screens that hid multiple dodgy activities by governments around the world. That said, it is inevitable that further regulations and legislation will be implemented; and once there is more clarity in this area, it will open the door for many new investors, as well as bring much needed clarity to current investors. Some governments have already laid out their position, at least for the time being, but many are still on the fence with the details.

https://bitcoinmagazine.com/articles/cryptocurrency-regulation-2018-where-world-stands-right-now/

4. Ponzi scheme rhetoric is an undeniable factor, painting Bitcoin as a huge bubble, ready to burst at any time and screw over the newest investors. This theory gets publicized every time the market experiences a drastic drop, but then disappears as it rises again with the naysayers muttering away. If you google Bitcoin Ponzi scheme, the first page contains only one positive article stating Bitcoin's case (actually a decent article by Miguel Cuneta - link below), the rest are all shouting as loud as they can about how it has all the tell-tale signs and should be avoided.

https://decentralize.today/bitcoin-is-the-total-opposite-of-a-ponzi-scheme-heres-why-4d795f0ed

5. Is it a real currency? Majority of people still see Bitcoin as an investment, not as an actual currency. Although growing, the number of businesses that accept Bitcoin as payment for their services/products is still tiny. As the number of investors increases, the volume of businesses accepting it as a form of payment should organically rise with them. Here is a worldwide map of businesses that accept cryptocurrency as payment, updated by the community, you can pinpoint businesses in your local area where you can spend your Bitcoin on regular purchases. The latest count on the website is over 12,000 businesses. There are other links available for multinational companies, but I thought this one was more interesting.

https://coinmap.org/

6. Difficult to purchase without having some knowledge. It is still daunting for the majority of regular folk out there, with too many hoops to jump through; and when the slightest mistake can cost you money, it is a risk that many are not willing to take. This is definitely an area which has to improve before the era of mass adoption can begin. As purchasing becomes less complicated, the number of people on board the the train will undoubtedly increase. It hasn't been helped by regulations restricting how/where/who can purchase it, but this should improve rapidly over the coming months/years as the process becomes more streamlined. Whether this will mean less verification documents required, or possibly even a new international form of identification aimed specifically at this area, is another question. Either way, it is definitely an area that needs work.

7. Lack of knowledge about the technology behind it. It is common sense, and I guess not really arguable, you shouldn't invest in something you don't understand. Unfortunately this is something that is unlikely to change for many people, as they do not have the inclination to put in the time to research it. As the other concerns are alleviated, this will gradually change, and for the younger population - maybe the under 30's? - the learning process should slot nicely in with the massive advances that technology has made during their lifetime. With babies navigating iPads, and pre-teens hacking government websites, cryptocurrency is a natural progression.

8. Hackers and security in general. This is probably the most relatable concern, as it affects old and new investors alike - especially my dad. Security of investment is an essential element when consumers are deciding where and how to store their assets. Houses and cars have alarms, but still get ransacked or stolen. Stores and banks have security guards, but still get robbed. Basically, there will always be someone out there trying to steal 'our' hard earned money, the key is protecting it as much as humanly possible. Obviously the method of protecting our cryptocurrency investments is completely different to the way we protect our physical assets, but the basic theory behind it is the same. This is where the average Joe gets confused, they don't see it as a direct comparison, but once these fears can be allayed (or at least seen as similar to protecting other assets), it will be another tick in the box. Heavy investment and improvement in cyber security by the industry itself, especially for exchanges and online wallets, will be an ongoing issue that will not be slowing down any time soon.

I'm sure there are more reasons people/my dad choose not to invest, but the list above likely covers the majority.

Personally I still haven't decided, but think I'll be in for at least the next couple of years. I want to be creaming some profits off the top in the meantime and diversifying my investments, but want to keep some skin in the game for the long haul too, especially with the projects I see have more of a long term vision. So far, I have not taken any profits out, just moved them around.