If local options aren't a fit, expand your search to other markets with strong rental demand.

Also, coming from running a business just think of RE as a business (which it is), the numbers have to work and your investments need to fit into the big picture.

thanksRyan  @Ryan RuppertShopify is a great platform for e-commerce, but it might not be the best fit for managing STRs in the long term.

I have tried pretty much anything personally and I have seen so many investors start and either succeed or fail - well, let's call it abort and sell to never touch RE again.And then I get calls from OOS investors who want to buy a 120k duplex in Milwaukee and when I try to tell them what will happen they go: uhm, I don't think we are a good fit.

That could totally be based on execution failure, but for us, it just wasn't a good fit. 

Right now, your fighting saying this square peg won't fit into the round hole. 

I designed a little U-shaped kitchen to fit right in the space.

I'd start by refining your search criteria, researching the surrounding markets, and comparing them to what best fits your needs, etc. 

It was honestly luck, I didn't know much about real estate I just knew I needed a house that was unappealing to others to be able to buy it and have it fit in our budget.

If you're planning to rehab properties for rental or flipping, a hard money lender might be the right fit.