And of course, if your actual cash value is less than the current mortgage(s) on the property, all of the cash value payment will go to the lenders. 

This is the current link I log into: https://bidonhomes.com/notes/l... 

So your debt is currently $3000 per month and your property earns you $1000 per month? 

I’m currently working on a deal in Fort Lauderdale & actively looking for financing solutions like hard money or private lending.

Quote from @Roger Flot: I was reviewing some renovated listings in my area and one indicated that even though the house was originally built in 1920, because of all the renovations bringing the house to current code, that you could get 2024 rates on insurance. 

I mainly bought it for the land, do not intend to rent it out for cash flow or what not.It is currently occupied by the previous owner.

If you find someone at a REA or other investor meetup group that is currently in this space it can make your first time go much smoother. 

However, if your time is limited or you don’t want to deal with tenants directly, hiring a property manager can make your life much easier—just be sure to choose one with solid local experience.Are you currently house hacking in Chicago?

I look to achieve the 1% rule when purchasing although in the current market it’s not a guarantee of cash flow.

Simply gifting him half the property now wouldn’t immediately allow him to claim the exclusion without fulfilling this residency requirement, I don't believe.One thought would be to use a HELOC to pull just enough equity out of the current home and use it to buy a smaller home, or at least the down payment.