I'm doing the same thing, although with no family.
In August I'm heading down to Uruguay and getting permanent residency. The paperwork required hasn't been bad so far. I only needed to sign a few documents and get my birth certificate legalized. I've got a lawyer assisting me and helping handle my appointments (including a medical checkup) once I arrive. The law firm's website is www.fs.com.uy/sitio/en/
One thing to watch out for is that Uruguay may start taxing income (domestic and foreign) for residents who are there longer than 183 days of the year. That's why I'm also going to get residency in Paraguay (no income taxes and not much more difficult to acquire permanent residency).
The guy I'm using is in Nevada, and I just started with him. So, I don't know that I can really "recommend" him. But if you don't find someone local, and would like to get his contact info, just send me an e-mail (address is in my profile).
In all seriousness, if you think that paying for tax advice is too expensive, wait until you see how expensive it can be when you don't get that advice. I've "been there, done that, paid the outrageous IRS penalties and interest" (I'm assuming that you're a U.S. citizen).
I'm currently in the process of setting up a new company and opted to pay an accountant on a monthly basis. It's going to cost me $150/month to have him handle the books for my fairly small business and ensure that I make the right payments at the right time. I probably could gone have gone even cheaper by paying for him to do some initial setup for QuickBooks and handling much of the rest on my own (with his occasional help). When I hired him, I told him exactly what my business goals were and how much I expected to make. Then I had him tell me what was the best way to pay myself. Ask other business owners you know for recommendations, if you can't find someone who charges a rate that you can afford.
I've been told that the IRS can crack down on you if you don't pay yourself a "reasonable" salary (which would require paying Social Security and Medicare) and only/mostly pay yourself through distributions. I consider the $1800/year that I'll be paying as cheap insurance against getting hit with a 5-figure penalty some time down the road. Plus, I can spend more of my time focusing on income-producing activities.
I'm working on my browser-based game (kind of like Kingdom of Loathing, but with cavemen) at http://www.shinyrockhunter.com and a more business-focused product that needs a bit more work before it's a minimally-viable product.
The Goal by Eliyahu Goldratt and Jeff Cox
How I Found Freedom in an Unfree World by Harry Browne
Even though "The Goal" is a story about process improvement for a factory, I've also used the thinking from it (basically, lean manufacturing) for software development.
I've also been using eLance for work on a project I've started, and expect that I will continue doing so.
My criteria to decide what work to outsource is "will having someone else do this task make a significant positive impact on the project". Generally, I've been doing the coding and outsourcing things that I don't do well (e.g., graphics and certain content). However, I'll probably hire some coders since that should let me add features significantly faster than I currently am able to do.
I'd strongly suggest starting out with outsourcing small tasks at first. Not only to protect you from paying a lot for work you may not be happy with, but also for you to decide if the results produced by someone else are so much better than what you could have done. My artistic skills are bad enough that paying an artist made sense. However, paying an editor to go through the site is probably something that I won't do again (since the gains weren't that noticeable).
In August I'm heading down to Uruguay and getting permanent residency. The paperwork required hasn't been bad so far. I only needed to sign a few documents and get my birth certificate legalized. I've got a lawyer assisting me and helping handle my appointments (including a medical checkup) once I arrive. The law firm's website is www.fs.com.uy/sitio/en/
One thing to watch out for is that Uruguay may start taxing income (domestic and foreign) for residents who are there longer than 183 days of the year. That's why I'm also going to get residency in Paraguay (no income taxes and not much more difficult to acquire permanent residency).