@Hakeem Valles I agree, we'd love to rent just to military members, but what is hanging us up is you can't turn a regular civilian away if they're qualified... And totally agree, I'm hoping the agent can shed some light with the flip option on what the true ARV of the property would be after some updating.... The hard part is neither of us are in a position to be in the area and touring the properties, we're long distance at this point so we're relying on our agent.
@Stephen Burke Agree - the Watertown area is full of multifamily houses and the bases keep the demand for renters up (even though there isn't too much else up there besides the base).
@John Warren I agree with the multiple exit strategies...in my mind it would be easier to sell a single family home (albeit a small bungalow) than a multifamily in most circumstances and get your money back because you wouldn't necessarily be selling to another investor. Just as you said, as for where we want to be long term, after his two years we will likely end up selling the NY property in an effort to consolidate our portfolio closer to where we want to be long term in the Delaware area.
What I wonder is it a good idea to try to live in flip with a low potential profit margin or buy and hold in a potential risky area to live for basically free? Or is it better to rent in NY for the two years and start looking for investment properties elsewhere closer to where we want to be investing long term (I guess another downside here is that you can't use a FHA or VA loan)?
Thanks again everyone for weighing in - after thinking it over so much it's great to hear what other people are thinking.