Some repairs are considered normal wear and tear, eg. depending the length of the tenancy you might not be able to charge for painting the interior of the house, cleaning (or even replacing) the carpet.

I normally do move-in fees in place of security deposits here in Chicago.

If the owner is not wanting to share critical information then you are gambling. 

Is a 40% equity stake normal, or a good or bad deal?  

I am also primiarily not a rental agent, so when I call it's normally a favor for a friends kid or something and I am just looking out for their best interest.

@Dave Hurt normally hosts a Charlotte Meetup of Biggerpocket members at the beginning of the month so be sure to keep a look out for it.

Hopefully, you'll also get the "walk through checklist" - in the event this tenant left the property in "less-than-similar" condition to when moving in (Note: You cannot deduct for "normal wear and tear.")  

And if you itemized and have receipts for all deductions taken, then it just comes down to the judge's decision on whether you are taking money from the deposit for what might be considered normal wear and tear vs damage.Maybe @Chris K. can weigh in with his opinion.

I think the audience for that kind of home is much smaller than normal - which means more holding time at ~$100/day carry costs.

I normally look at just getting new financing at purchase, but wanted to consider this option to assume current loan to see if it would be worth it.