The removal of the Taxable Value cap and the switch to Non-Homestead millage rates can double, even triple, the property taxes.

I removed the chimney and added modern HVAC, making it the only house on the block with it, significantly enhancing its value.

I removed the chimney entirely and installed a full HVAC system, making it the only house on the block with modern heating and cooling.

I have had to escalate review removals and broken items a few times and they always drag their feet on it. 

Property appraised for 620k earlier this year after the ADU construction (appraised it to remove PMI) and I owe $375k on the mortgage + 59k fixed rate second.

Your calculations should include utililies and repairs, legals, snow removal, etc.

If you need to invest in $5k or $10k increments chances are strong you will need access to your money on your timeline, not some syndicator or someone once removed from the syndicator says you can have your money back..

I personally don't charge for small holes and touch-ups unless they are grossly excessive, but I would charge for removing the tape/adhesive.

.), removing tenants and marketing to new tenants.

I would owner occupy it so I don't know if I have an avenue to remove them so I can do the condo conversion or if I could even do the condo conversion while they are still in there.