Also, pricelabs does not include cleaning.  

The wholetail is a smart play, but you should be cleaning the place thoroughly and doing no repairs and then presenting an honest proforma with rents and expenses estimated so investors have a PDF to look through.

We are concerned that the smoking/smell will turn off prospects as well as the extra cost of cleaning up areas after smokers move out.The building is in Illinois. 

Or just clean up the loans to get them into a single loan?

What you can do right now is connect with an investor-focused real estate agent who has house hacked before or is house hacking now and routinely works with other house hack buyers.

We both have high W-2 income and own all our properties clean and clear.   

10% is probably a little steep, and like John said, a flat fee may be more reasonable.Setting up a proper STR is not cheap, but once you are set up properly, you deal with routine breakage.I recommend managing yourself and saving the 20% personally, getting a rockstar cleaning team and a reliable handy person, using something like Hospitable that can help automate messaging when listing, and reading the book from the bookstore here called Short-Term Rental, Long-Term Wealth.

You will clean it out, but for that, you need to get it at a lesser price, bargain basement because this place is dangerous.

I can see a full day of labor, between getting supplies gathered, setting the job up and also clean up and disposal.

Given, I'm a nice person and a clean roommate (LOL) but they don't know that.