Tenancy in common gives more control over what happens after death, allowing you to specify beneficiaries or sell your share separately.

I'm also not a system matter expert and don't want someone trying to sell me something that is not really needed. 

Deciding between selling vs renting out a single family with 5 bed/3.5 bath.

Even if they decide to sell before the assessment hits, good buyers agents will always request minutes or management to disclose any assessment discussions.Third, there is more and more rental buildings in Miami that can be as affordable as old / smaller condos.

If the property does not debt cover, you may want to consider a no ratio loan, qualifying with a bank statement loan, or just selling the property all together. 

My 5th and final mistake: Not having absolute clarity on wanting to BRRRR it or sell it.

I got a new job out of state and the property has appreciated to 350k and we are looking to sell and move.

In NY it will take 70-90 days to get a mortgage turned around.Fake numbers:* Purchase: $400k* Fees/Transaction Costs/Repairs/Holding: $200kAssuming equity requirements are 25%, you'd need the property to appraise/sell for 800k to get your 600k back out (and return to the lender). 

So I think it's safe to say that unless the hoa agrees to me turning it into s8 (which I doubt) the units will be in a s8 area which may keep the selling price low if I ever need to sell.

A traditional sole ownership property will cost you approximately 5% of the total value of the property to sell based on fees we are all used to paying (and you are paying all of that out of your equity, regardless of how much debt is on the property, and without a return of capital clause).Again, simplify your analysis to a strict understanding of the property level analysis inside the portfolio - something you've likely been doing on your investments to date.