Quote from @Jeff Roth: Hi Lina from Texas-Congratulations on your interest in investing in mid-term rentals and you are wondering how and where to get started.I get this question frequently from investors.Sometimes and investor is looking to keep their property cashflow positive as insurance and taxes have squeezed cashflow by turning units into mid-term or short-term rentals.First off, ideally, the property will cashflow as a long-term rental should something disrupt the mid-term rental model.You will also want to have the property be near where there would be a demand for mid-term rentals (hospitals, universities, research centers).Monthly rents for mid-term rentals are about 20% (+/-) higher than unfurnished similar long-term rentals.There are property managers that will manage mid-term rentals for you and I always advise my clients to use property managers to keep their investment as passive as possible and for compliance issues related to Fair Housing Laws and local regulations.To Your Success! 

@Andrew Self there are attornies you can hire to resolve your credit issues.

I'm also having issue with no onsite manager, but in regards to insurance. 

This is less of an issue here that what you all are describing.  

Not having them can create issues when selling later.Over-improving for the Neighborhood – Be mindful of your area’s home values so you don’t invest more than you can recoup.Ignoring Structural & Mechanical Issues – While cosmetic updates are fun, addressing foundation, plumbing, electrical, and HVAC systems first will save headaches down the road.For the best return on investment, focus on:Kitchen & Bathrooms – These are the biggest value-adds for a home.

However, our tenant turned out to be problematic—late payments, issues that led to an eviction, and additional repair costs before we could relist the property for sale.Now, after months of making mortgage payments out of pocket, we finally have an offer.

Finding borrowers won't be an issue, so I wouldn't worry about that piece, just making sure you have an agreement you are comfortable with and borrowers and properties you are comfortable with.

I know people who do this and I do not believe there are issues with it, but speak to an attorney and they should probably notify the company if they are an employee of that company that they are doing this.

Given the scope of your work, a simple plumbing leak would not concern me, it's a $200 issue at the most and ideally, it's just another line item when you do rough in plumbing for the kitchen.Being in a Milwaukee suburb, I am guessing it's a 1960s ranch, probably with galvanized plumbing.

If the commercial space isn't too disruptive, you shouldn't have an issue renting an ADU up there.