A little late on the reply but I own property on bay rd in bonita springs directly across from the gulf but I was able to have the owner transfer his floor policy to me.  

Don't forget to subtract selling costs, transfer tax, and interest payments to arrive at your "true" profit.

Is it ok for me to transfer money from the llc to the personal checking?

If you decide to move those funds into self-directed IRA as @Amanda Gust suggested - there will be no tax or penalties associated with the transfer since it is be considered Direct Rollover.

If you're handed the keys to the landlord then you've legally transferred possession.

Yes, and same with the property, the buyer can cloud title and tie up the transfer of title, thus tying up the sale of the property too should a seller try to take a deposit under bad faith.  

My only thoughts are this is probably mostly an appreciation play but also, that $40k in appreciation, how much of that is eaten up at closing in 10 years by commissions, transfer tax, other closing costs, etc.?

I’m looking fo options to purchase under LLC without having to later transfer to a trust.

Your existing lease transferred with the sale of the property.

That typically only occurs after the tax sale process fails and the lien(s) must be abated in order to transfer to a new owner.