We arrive in Portugal at the end of March and once we have got ourselves sorted I will see if we can get a few people around for a meet up. 

Dave NA ,Non LLC and non corporation husband-wife holders of rental properties do not have to file a partnership return; They can file Schedule E.The problems comes if it is held by an LLC(Two-member) in a non-community property state.For the management activities I would still recommend using an S-election or C-corp if applicable.

@Chris Kay finding a quality, cost-effective contractor is extremely difficult:(There are thousands of contractors that are great talkers, but rarely perform within budget.Standard bait & switch is to lowball a bid, then once they get started all sorts of things "pop up" that somehow their bid didn't cover.

Unless you have some sort of subject matter expertise or access to an unfair advantage (cheap labor, ways to source off market deals, etc.), index funds are likely to provide an equal or better return with a MUCH lower hassle factor and more liquidity.

This email gives people yet another opportunity to self-select out of the application process based on my expectations and criteria before an actual showing in scheduled. 

I have $25K cash for a down payment and can add $20K/year ($1,600/month) toward payments.No W2s, I've looked into building a small home right away and using a bank statements loan (have about 8800. monthly income) , but with 9%+ interest rates, it’s beyond my budget.Is there any sort of creative financing ideas possible or private lender possibilities?

I know that varies but he just has selective empathy.

Most reverse exchanges are done with cash from the client or a private loan of some sort from an individual or a portfolio bank.When your old property sells you will have that cash in your account to purchase the new property. 

I think there’s some sort of option of to do a little refi on both house 1 and 2 and get the money needed to wipe out the line of credit(allowing for bigger flip opportunities, especially if I partner up with someone) and also renovating that garage space with the private investor as long as it is under 1000/month.

That sort of difference in expense with turnover/vacancy means that the approach to tenant retention means something different to the business.