Just called an appraisal's office and asked the question, kinda got an answer I wasn't expecting.

You are not expected to take “heroic” steps - just a reasonable attempt to return the deposit/provide an itemized statement on its disposition.

In his better days, my friend was doing self-employed HVAC, and I know he's decently handy, so he probably has some expectations regarding compensation.

We expect the house to resale for $650,000+.  

If you have to go buyer leads—expect it to cost more and you’ll want to create a couple “lead magnets” like free “how to sell in 5 easy steps your house guide” or “Inexpensive upgrades for a huge ROI on house sale price” or something like that to incentive people to fork over they’re information or like your page.

I'd expect that the excess mileage charges would be a killer.I think next time I'd so something like a Jeep or a Honda SUV. 

I expect some issues with flat roofs in the Chicago area, and can tell pretty quickly how much trouble they will be. 

I have never owned any of these before and am curious what I can expect with regards to renters.

Showing and explaining the troubles we all can expect to run in to.

That being said, ADR * Occupancy Rate is the quickest way to get an estimated GOI (gross operating income) from which most of your other expected cash flow and accounting calculations are going to flow from.I was going to tell you about a guy I read about that was creating an app for something similar to what you are talking about, only to find that was you