There’s a book called the house Hacking Strategy, it’s pretty solid. 

@Boffill YosleysFeel free to PM I can send you some solid contacts :)

Solid post! 

But you don't want neighboring STRs to get all the bookings while you're off the market, unless the demand is so high there that you think you can get higher prices and be solidly booked with late bookings. 

Your past experience with sneaky smokers is a solid teacher.

I understand that paying off a property means positive cash flow once rented.  

You will both learn that there is more to a safe loan than a note and deed of trust.In no order, typical loan documents will include: NoteDeed-of-TrustPurchase Contract and escrow instructions to confirm your deal and the associated deadlines you and your lender will have to meet.Preliminary Title Report, which you and your lender should learn to read to understand all liens against the property.Personal Guarantee (You do want to protect your lender don't you?)

That is fine if you understand that is road you are going down.

Tampa for a solid STR strategy and appreciationTampa Bay is Zillow’s hottest housing market for 2022

From what I understand so far is the steps below:1) The rules and procedures are exactly the same for all counties in IL as it is a state law and does not change from county to county.