In general, it's better to have the team work closely together in one office. If you want to bring in contract developers they should be reachable during the time when you work because you'll probably need to communicate very often. So, the timezone difference shouldn't be too large (USA - Europe is probably too much already, at least for your main developers). Later you might want to have a backup developer in a different time zone, so he can troubleshoot problems while you're sleeping. Also, when outsourcing it would be better to pick someone (or a team) with startup experience.

Is the startup experienced hire more flexible? Yes, its funny, with a bitcoin business, I'd imagine there is no business that gets port scanned more often. Everyone's probably looking for a hotwallet. I think I can mitigate that with deterministic wallets and or pre computed pools of watch only addresses. Both of these solutions would result in private keys never seeing a network.

So for hiring devs in the philippines, it seems that there's no hits for the word bitcoin in the searchable job resumes. Any tips on what other keywords I might be using? Node.js and javascript if we use any of the bitcore.io stuff? A database guy, a full stack guy? I think 3 guys can get the job done in a reasonable time frame. Chain.com could likely take much of the load off the backend dev.

At a loss as to how to choose 3 programmers from a sea of programmers with job applications ready for hire.

I would lean towards hiring devs, even if remotely, as opposed to outsourcing.

Especially if your startup may be handling users' private keys, you will want a trustworthy domestic dev team. The last thing you want is millions of dollars (or bitcoins!) worth of your users' deposits to disappear without a trace overseas.