As a SFR investor for over 15 years I have been wrestling with this question in the past, because it feels like you should upgrade to "bigger".I know for sure that I would not enjoy the ownership experience that comes with a small 4F, because in Milwaukee that typically also means lower income tenants. 

Quote from @Amir Portal: Hi friends , i Would be happy if you could guid me from your experience on where to start whit a strategy of BRRRR in DFW

Does anyone have any experience (or know someone or a company that might) be able to demo a concrete staircase Ana turn it into a driveway and ADU ramp ?

Secondly, you'll definitely want to confirm with a tax strategist with experience in the STR space to confirm if the setup you describe will pass as an STR with the IRS. 

Sounds like you’ve got some solid experience under your belt.

I’ve heard of a few different options but would love to hear your experiences, especially if you've used gap funding on flips, new construction, or commercial projects.

Actual experience I'll listen to.

I’d really appreciate the opportunity to learn from those with experience.

I am starting to realize there has been a significant amount of consolidation in the space by private equity and other institutional investors. 3) From research it also seems like getting financing can be difficult without prior experience in the space.

The better the rates, lenders generally want to see more experience, higher credit, occupancy and DSCR requirements.