Yes you are buying near a peak and over paying for the area you are in, but if it meets your family needs and you are ok with those negatives then pull the trigger. 

Do I need to disclosure or wait till it triggered itself?

I’m just very nervous to pull the trigger on something like that given the volatility of the market right now.

That being said highest and best does not necessarily mean the newest nicest stuff within.If it is in NEED of replacement in your eyes then pull the trigger just make sure you are in line with the area and your market rent supports. 

I see it more of an asset then in investment, needless to say I pulled the trigger built a family. three years later Ive had a great place to live and I'm getting out with money in the bank.

Yes, Fannie Mae changed their rules on 6/1/2016 to now allow a borrower to transfer title to an LLC that the borrowers on the loan are the majority members of, without it triggering a due on sale clause.

I'm about to pull the trigger on a house hack this month, it's exciting! 

If your property is financed, then moving it directly into an LLC will trigger a transfer tax in Florida. 

Fannie Mae changed this rule back on 6/1/2016, and it will not trigger a due on sale clause now.

You have to be careful not to trigger the Mortgage payoff in full, clause, until you are ready to pay it off.