Outside the U.S., what specific obstacles does Bitcoin face for hobbyists and small entrepreneurs wanting to enter the space?

Barring the legality of Bitcoin in various markets, which in itself can be a pretty large deterrent, there are a few factors which hinder the growth of Bitcoins. In no particular order:

• Buying Bitcoins. Though on the surface this may seem like a non-issue to many, it is most definitely an issue. If someone is going to suggest LocalBitcoins I would cite, get real (no offense). The rest of the world really doesn't have enthusiasts meeting up in cafes and buying/selling bitcoins. The very few markets in which there are local Bitcoin sellers, they charge an arm and a leg. If an enthusiast has say $500, for them to try to send this money over to an exchange like Bitstamp or BTC-e, etc. means wire-transferring the money. Which is a hassle, costly (the regular fees is about $25-$60 that would be deducted) and only then would the enthusiast be able to buy bitcoins. Making the buying process easier by providing local payment options (somehow) is much needed. This gets more complicated when you have to deal with a market in which Bitcoin is not legal &/or money movement is very restricted.
  
• Accepting Bitcoins. Very few merchants would be willing to accept bitcoins. There needs to be some form of an evangelism movement on ground to educate and on-board merchants for Bitcoin acceptance. Without such a drive by which they are educated, merchants will not figure out by themselves the need to accept Bitcoins.
  
• Localized Bitcoin Retailers. Whilst Circle, BitPay and Coinbase are excellent initiatives, they are mostly focused on US businesses. If there is a Bitcoin retailer who is willing to work with the developing or emerging markets in South Asia, Africa, South East Asia, GCC, etc. this will have a huge impact. The tough part would be in the understanding of documentation and other paper requirements for the purposes of KYC/vetting, etc. but this is not an impossible task.
  
• Localized Payout. Its great to accept Bitcoins, but when it comes to payouts in the local currency, chances are most of the exchanges or even Bitcoin retailers have limited offering as far as XBT and associated currency pair is concerned (mostly XBT/USD, XBT/EUR, XBT/JPY, XBT/GBP). Bitcoin retailers can use FX companies to offer a larger payout basket. Yes, this would be double conversion, but until and unless a Retailer in say Dhaka is not getting paid in Bangladeshi Taka (BDT) locally, there is little incentive for the merchant to jump onto the Bitcoin bandwagon, regardless of the ruckus.
  
• Connectivity to local Payment Rails/Banking. This is a tough one. But if local Bitcoin hobbyists can pay for and and get paid out using the local payment/banking rails, it makes life simpler and easier for them. This can be challenging in most markets that either have a no-action on Bitcoin or have made it downright illegal to trade with.
  

If the above mentioned points are addressed, and they are not too difficult to solve, the local Bitcoin market adoption and trade is bound to increase. Most hobbyists that I have spoken out to feel they have been alienated by the bigger Bitcoin companies, they complain "no one is looking at us".

I think it is time we turned our direction towards them.