Sounded like there was heavy paperwork involved.  

Companies that know what they're doing don't get involved with the race to the bottom. 

For example, you might agree to a 70/30 or 60/40 split, depending on his level of involvement.

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

Then there were some issues with the inspection report that ruined 3 contracts prior to me getting involved.

It may be easy to rectify, maybe not, depends on your jurisdiction, the issues involved and the City's stance. 

Lastly more to my point - I thought you worked for a MF syndication in the past that I was not sure but wanted to mention and that you are not just someone coming off the street having never been involved in a deal (unlike a lot of others).  

I think it speaks volumes regarding your care to the situation the heir is involved in.

I am very involved in our local real estate investor association and agree that in this central Florida market there are an over saturation of STRs as well.

I would tend to agree with the other CPAs typically.The 500-hour test is one of seven material participation tests used by the IRS to determine if a taxpayer is actively involved in a trade, business, or rental activity.