This helps cover the time and effort in overseeing the work.

Was this a typo or do they truly only cover RET and Ins, but no maintenance?

Doesn't even cover the full mortgage. 

In the later years he moved upstairs into the 8 room apartment and the rent from the stores more than covered his retirement.

Still cashflows a lot and uses debt responsibly to expand a little faster.I'm curious what you are looking at when doing a deal similar to this to make the right cash offer of not too little but also not too much when thinking strictly in terms of cashflow.My analysis must cover the payment plus $1,000/month if I'm using leverage.

Since there's a chance I might move away in about 3-4 years, I want to make sure I can rent it out later and cover all my expenses with the rental income.Can anyone recommend areas in downtown Chicago that would fit my criteria and might appreciate a bit over time?

https://www.biggerpockets.com/blog/best-college-markets-for-...We cover this and more in our weekly BiggerStays newsletter, which is for all things STR.

First protection (the one you need to cover you in court) is no sublease in the contract: in FL, it's the standard option. 

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Currently the rent from the tenants covers all our expensed.