@Everyone, I apologize in advance because this is going to be long (though not as long as normal because I can cite my own rants now).
First and foremost, as a fellow military member, Javier Molina, Thank you for your service and good luck with your Real Estate investment prospects.
Next in addressing Simon Campbell, Your info regarding multiple VA loans is not entirely accurate. I explained the possible situation where you can use multiple pulls of a single VA eligibility without paying off your open VA loans - http://www.biggerpockets.com/forums/12/topics/86709-help-analysis-paralysis
It's the last post in that thread. I think there is information there that might help Javier as well.
Next some advice, Javier, it sounds like you have an idea of what you want, but you aren't sure how to execute. If you want to live in a place and then rent it out do that. If you are planning on trying to do this for a living, you want to make sure you get the best deals out there. It's important to know early on if you want to go into multifamily properties or single family homes. While it is true that you can get more rent (typically) for multifamily units, you run into issues with financing, as well as several other potential local problems. For example, here in Ohio, I have a friend who owns a duplex, they were trying to do simple renovations and run a new drain pipe but the city they are in requires anything greater than a SFH be considered a commercial property and requires commercial contractors. So they literally had to hire a guy for $500 to supervise their contractor to do the work because all the commercial contractors come at a commercial price point. So that's just one potential issue you might end up with.
You can look back at past posts (including the linked one) and see that my goal is to buy where I'm stationed at "if it makes sense". It sounds like you have a good justification for buying there but I really like to have my houses not be completely reliant on the military for their income. If there is defense industry or other major job sources that makes me feel more comfortable in my decision making process.
Brian Mathews, I know know what your background is, but if you don't have military experience I would highly recommend not giving advice regarding military specific issues. For example, I have found very few locations where it was actually a good deal to live on base. Most bases, privatized or otherwise, set the rent to be all your BAH and then you have to pay a reduced utilities rate. BAH is typically 70% of the local markets rental value (depending on where you are) so it could easily cover a house off base and all utilities, and it typically can cover most mortgage payments assuming you are buying at your income level. Furthermore, living on base housing doesn't gain you a better house. My last base they were in the process of condemning the base housing because they were that old and fallen apart. AND I had a buddy that was living in housing, they held his security deposit when he left because they said his carpets were not clean enough. They were demolishing the building! And when you sign a contract with most government housing you lose or severely reduce your right to recover your money via the court system because the way the system is set up.
Everybody values their risk decision individually. This includes the long distance land lording risk and the property being vacant. You have a great positive going for you in if you go VA you will be owner occupied for at least a short period of time. What this means is you can meet the neighbors, grow a relationship and build a network of people you can trust to oversee your property while you are gone. I have contact info for 3 different people around my California property, and I'm building that relationship with a few people here, we have a nice church leader that is a neighbor who is very happy I've been keeping up the house because she grew up in it 30 years ago. You don't get that kind of interaction during typical investments but its nice knowing people who care are around.
And finally, I have to mention your potential tax liability. California, in their infinite wisdom, has decided to impose a 7% franchise tax board tax on rental income going to out of state investors that use a property management company. This is in an effort to ensure they can collect as much as possible without dealing with silly things like deductions etc. There are plenty of forms to fill out in order to get a reduced or waived withholding, but rather than just filing your taxes minus depreciation/expenses at the end of the year, you would get hit quarterly unless you self manage. If you self manage, you don't have to follow that route, but make sure you know the tax issues. Because you are moving around a lot, it would probably benefit you to hire a CPA in every state you have a property to manage or get real smart on tax codes otherwise you could get a nasty surprise since most CPAs wouldn't think to look into this sort of thing. If you think about it, the way they implemented the tax it's brilliant. They tax you through a Property management company, and only out of state investors. That means your local CPA won't know what the right code is and most California CPA's wouldn't know it because it only affects out of state investors and. Enough about that, but just make sure you know what you are doing before you get into it.
Thanks again for your service and sorry again for the long reply.
Sincerely,
Jason Minnich