I've also been in finance for the last 5 years and I'm extremely data and number driven.

Talk to the necessary people to ensure you can get a loan if needed.Many people are stuck here - not because of lack of resources - but simply because they are just CONFUSED about their financing options.

Sounds like you're missing key information by saying "I don't believe I will be eligible for a traditional loan".... get that piece of data by applying for a loan at multiple lenders before assuming you can't.

I'm currently narrowing down my Townships and trying to scour data/street views/physically walking + driving through prospective towns.Look forward to reading some of the responses, I especially want to learn from your mistakes!

If this seems feasible, ensure you have a lawyer help you with the contract details.

Don't look at this as a negative..yes it is a pain, but they are ensuring that their "investment" is being done correctly.

Don't look at this as a negative..yes it is a pain, but they are ensuring that their "investment" is being done correctly. 

I’ll look up what properties you have and as much information as possible with relevant market data and try to set an in person meeting.

Who is going to go to homes and ensure they have been winterized? 

In the long run, real estate is generally going to be a good investment, so just make sure the first deal is not going to undo you financially by ensuring to look at the worst case scenarios.