Our next step to proceed in this direction would be to hire a civil engineer to do surveying and site map and that engineer would also see if the creek in the back of the property affects build-ability.  

I understand that VA loans are assumable, but I'm unsure how this affects the original borrower's ability to use their VA loan benefits in the future.

You will be well-positioned to be successful as a real estate investor if you keep expanding your knowledge, abilities, and network.Good luck!

South Hillsboro has had the largest development in the history of the state but a little more expensive.Two years ago, the state legislature gave the governor the ability to pull properties out of EFU and in to the Urban Growth Boundary with the stroke of the pen

To summarize, alot of the issues you are experiencing can be mitigaged with proper contract management from the start as it offers the ability to understand staffing and the many relationships and contract participants.

How much is the ability to assume a loan at 2.25% worth? 

I have complete confidence in their ability to pay their share of rent but my concern is with the City's portion as I have heard first-hand accounts and bad cases where the City has delayed payments, delayed processing of renewal for voucher holder (and thus payments) and lack of communication.Are there folks here who have had a good experience with CityFHEPS and the City's ability to pay on time? 

It's free to list and had solid SEO.

I would utilize a local bank, such as Hills Bank or Green State, they have the ability to utilize "in-house" lending and can be a bit more aggressive in how they lend given the potential forced appreciation.

You would probably have to foreclose - a much more difficult process.A lease with and option will not negatively impact your ability to 1031 in a year.