Yes it is indeed rather hard to enter the bitcoin world atm. Currently you have to be tech-savvy, risk-loving, somewhat idealistic and have some money available to buy them (or at least stuff to sell). I think the sudden rise in value also put some potential newcomers off because they either think they have missed the train or they think it's a bubble/pyramid/scam/whatever.
It will surely help to have the fiat exchange rates to stabilize a bit because then both merchants and customers will gain more confidence using it like normal money and not viewing it as a high-risk speculative asset.
Mining bitcoins was a nice concept to get them distributed but with difficulty skyrocketing at current rates this will soon be a monopolized business and therefore we might have to think of new ways to distribute the coins to interested users.
Bounties are probably a good way, but chances are they are collected by the die-hard hoarders as well.
The faucet is a great thing but it has been abused and nowadays doesn't really offer you that much in return for a Google account.
Physical bitcoin-cards maybe a neat idea as a gift, but without explaining the concept (which can be a bit daunting for the average not-so-enthusiast) they are probably going to throw them away or just quickly selling them for $$.
A good idea is probably to have talks or booths at conventions where the concept could be properly introduced and people could get a small amount of bitcoins as starter-packs, maybe buy them at subsidized rates or better still: have some games with the chance to win bitcoins. This would be kind of a real-world faucet and could surely be funded by donations as well.
Another issue is the usability of the official client. I think the client needs much more work in terms of user-friendliness - it should ideally be self-explanatory, not only for its own usage but for the bitcoin system as a whole. Maybe even have something in the style of the "What is Bitcoin?"-video as a tutorial mode...
The other side of this issue is, that people will more likely want to overcome the difficulties to come aboard, if the incentives for using bitcoins were higher. Currently the great advantages of the bitcoin system are often not recognized by the average non-geek and I think we still have way to go in terms of using bitcoins to their full potential for the them.
One possibility would be to get them "one community at a time". Ok, right now we probably have a subset of the geeks, the gamers, the venture capitalists, the libertarians, the anarchists,... Anyone reading this who does not fit in, please stand up
But to go more mainstream we probably have to look at something like the music communities - bitcoins are a great method of payment for independent artists but we still need some good system for that. Micropayments are another thing which could be an incredibly well-suited use-case for bitcoins (given we sort out a few things regarding transaction-fees) and also used to get websites introducing their visitors to the coin.
I am sure bitcoins could be utilized to suit the needs of many different communities/interest groups and there is much work done but we're not there yet.
All in all, I'd say give it some time - let the market stabilize a bit, get more work done on the different online-platforms, improve the client-usability, sort out some legal issues for the merchants and work on new ways to incentivize users to come aboard. Sooner or later they sure will
