But ya have to make some educated prognostications in life.Add this to the information your processing - What your talking about doing is eliminating around $4000 or interest expense (which is deductible anyway so really could be a real impact of eliminating $2800 or so) of debt in exchange for paying over $10K in capital gains tax (don't forget possible state gains tax as well).  

A high property tax rate will increase the taxes more quickly as a percentage of total expenses when the property value increases.

I also know I can look at ways of borrowing against that equity (HELOC for example) but I also just feel like if I take debt on that property the cashflow goes down, and then if the association also takes the loan it goes down more, and at that point I don't know why it would be a better option than selling before August. 

Not really a tax question as the membership % decides who does, gets and deducts what. 

I have ZERO debts.

DSCR qualifies borrowers with rental income rather than personal income, so you don't need tax returns.

-Transfer the property into an LLC – This may allow me to take ownership while potentially avoiding property tax reassessment, however this sounds like an involved process-Establish a living trust for my aunt and mother – The trust would specify that I inherit the property upon their passing and provide step up in cost basis but i'm worried that the living trust can be modified to have me removed (who knows what can happen) - My mother is somewhat volatile.I would like to live in the property and my mother will live in her second property with her husband. 

We own 3 other rental properties that have a 6.5%-7.5% APR, and no credit card debt or any other high interest debt to pay off.

So I carry effectively 0 debt. 

Does seller have debt?