Money management has never been a big problem for me and its almost natural for me to live somewhat frugally but its a big number to have in front of you at such a young age and I would appreciate the advice from someone who has a little more life experience than myself.

Lastly, after you receive advice from other Chicago area SLH operators & the local municipal agencies that will not only save you time but direct you towards ways to save you money, you are going to likely want to register your business as an LLC with the state and obtain the proper small business renters Insurance policy under your LLC’s name (if its just a 2-3br operation the policy monthly premium  cost will be very low and will shield you as an individual from the very probable situation of being personally liable for the behaviors, damages, & actions of a traditionally high-risk short-term tenant group bc no landlord’s homeowners insurance policy will cover any damages or personal liabilities that will occur when they discover the nature of the operation.

And, naturally, there will be more paperwork, since you're starting from scratch in the eyes of that new lender (who does not care about your 40 day old pay-stubs, etc, they want the most recent ones).

I think it’s pretty dangerous to start generalizing these things due to the exponential nature of what a spreadsheet calculation mistake could cost you.If you already have a process in place it’s pretty easy to see what it would look like at different scales but that needs to be defined from the beginning.

The alternative is to accept the progressing deteriation, rent to inferior people until you can't rent it anymore at all.The median price point for a single family in Milwaukee is $192k as of September 2020.

Now a toilet clog or something of that nature would be more suitable.

It naturally makes it less competitive.

I see more buyers put off by "busy" granite than by a cheaper alternative. 

Pros: Good location that balances work proximity with a good area with potential for natural appreciation.

Second, if you're ever in doubt about a loan like this, look to see if the contract includes "underwriting fees" or anything of that nature.