STRs sound like too much work to me.Portfolio income = stock dividends, interest income (from banks, credit union etc), Master Limited Partnerships (Form K-1), Business Development Companies (Form 1099), bonds, interest earned from investing in a real estate debt fund, interest earned from being a private lender

For those who've made the leap, what has been your biggest hurdle?

All this to say starting is the biggest, hardest, most important step.

Biggest pati le is getting approved from VA and bringing property up to regulation.

So it isn't a complete waste, you would simply need to follow the strict reading of the law with no private clauses for consideration...I'm not sure how that plays out since technically if the lease is void, so is the tenancy meaning you could terminate anytime and not wait for the original lease expiration...I'm sure that's covered somewhere, but again I'd ask my local atty what to do given this is such a locally specific issue. 

Your biggest issue with 5 bedrooms is that 50% of your income is going towards the mortgage, I do not believe banks would even lend to you with a DTI above 40-45 (mortgage + other debts).

Biggest thing is adjust pricing appropriately. 

TIAErich your best bet would be to amortize it over thirty with a 5 year balloon. the issue with private lenders  vs. banks is private lenders use their money to lend and many times it may not keep up with inflation - so lending for that long does not make sense.

I'm looking for ways I can "protect" this private lender. 

The biggest mistake I made in my RE investing career early on was being so conservative that I only bought homes for cash, i.e.