I had a heart-to-heart with the contractor and made it clear what our expectations were and no more money (he was asking for a second payment of a three payment contract) would come his way. 

The appraisal district shortly thereafter corrected the tax allotment “anomaly” between the two lots, but the investor never made a tax payment and eventually lost the lot to a tax foreclosure.  

If you are going to be an owner-occupant, want a low down payment, and are planning to do a renovation, the FHA 203k and Fannie May Homestyle loans are your best optionsHow do you know the property is currently upside down on the mortgage? 

Use the 20K as a down payment on the next house hack and don't touch your current properties equity.

Some special assessments are already board-approved for 2025 and 2026 to help raise capital for such items, however I know when the time comes there will be a loan which likely demands a higher monthly payment for owners -- reducing my cashflow. - Based on sale of other units in the complex, I believe my current equity to be roughly $160,000, a little more than 50% equity. - The condo is currently leased through April 30, 2025. - August 2025 will be 3 years since I moved out.

I assumed you'd use HELOC for down payment + another loan for the rest. that is 100% financed. 

I understand the BRRRR method is not all that it used to be in the past years, but given that I have a lot of capital to play with, I figured that I would still be able to find ways to make it applicable.Does anybody have any suggestions/tips for me?

On the lease, he'll pay me $100/m over my HELOC payment and all other expenses, including the refi cost, inspections, title work, etc... 

I am of the opinion that you'd be better served using that money toward the down payment on a property.

Your payments are known.