Trading off current cashflow for principal payoff in the future?

There's always trade offs when it comes to investing and one of those tradeoffs (if you want to find positive cash flow) is having to be okay with an older house.

I think an equally probable scenario is that we'll convert it to a rental, and then look into a 1031 exchange if we think we can trade into a better-performing asset. 

You may see if you have one in your area that you could trade your property into something nicer. 

We have trades we use on jobs and know what they will charge which is often considerably less than what Joe Homeowner would pay for the same job . . . the trades know we will be using them again and again. 

By definition, these type of loans are not the same quality as what is traded on wall street. 

Some costs MAY qualify as startup costs if the rental rises to a qualifying trade or business level under 195 as well.

I want a specialist that's an expert, and not a jack of all trades and master of none.

And remember, the Federal Trade Commission warns against pay up front loans:  https://www.consumer.ftc.gov/a...Lendbase is able to skirt around this by claiming that they are just a "broker" and not the actual lender.  

It’s worth considering the trade-offs between the stability of income and the increased oversight and hoops you'll have to jump through.