I would pass on this deal given the red flags you share (and the fact you feel there are red flags is generally a bad sign).

I feel like that's a reasonable thing to ask before making an offer because that will affect the cash flow significantly. 

I feel like it would be easier to get bf out if they are both at risk of an eviction but obviously legaly questionable… I just want it empty :((Currently trying to get a hold of boyfriend for his side/plans/expectations)

When talking to property managers, ask questions regarding any guarantees they offer owners and refer to any online reviews to get a better idea of how tenants and other owners feel about working with the company.

But I feel like I don't know what I don't know when it comes to running numbers in the midwest. 

Don't feel the need rush the process and choose the first one that comes through.

Narrowing down a market can definitely feel overwhelming, but focusing on key factors like job growth, population trends, and rental demand can help.

Best of luck to you working through the renovations - if you need any design advice, feel free to reach out!

Are people holding on to their money or are they feeling good about the future?  

Feel free to DM me if you want to talk more.