But, they will be in challenging parts of town where realistically you do not want to own property and your long-run returns will under-perform.I'd encourage you to find a balance of sub-market growth, nearby employment, strong income, and only then a good rent-to-value ratio. 

I charge a good bit for my properties, that screens them.Do hotels run background checks on guests?

If I ever run low on reserves, I can easily transfer funds from my personal to rental account.

A competent CPA can save you more money than their fee, making it a wise investment in the long run.

@Sarita Scherpereel runs meetups in Chicago so she may be able to point in the right direction.

I am not exactly sure what my goal is for the long run, but for the time being I'm looking to get a roommate, then after 2 years, to fully rent out my place and hopefully get some cash flow.

Quitting is a head trip and it takes a while to wrap your head around it but life, just as in retirement, is what you make of it.So, how are you doing it.

That being said, anything can happen, but if you run your numbers accordingly, make sure that your contractor is trusted and do all the other stuff you'll be a little more protected than the next person flipping that does not do this type of calculation. 

Has anyone run into problems with this sort of lending?

I’m eating breakfast and adding thoughts as they pop in my head.