I'm a property tax professional (reducing taxes for commercial property owners) living in Northern Kentucky.

Stocks are pretty liquid, BUT selling them triggers tax consequences and the timing of when you want the money for real estate purposes might not coincide with the best time to sell the stock.

Hire a tax professional to help set everything up. 

You can do a 1031 exchange and use those funds towards another investment purchase (basically a tax deferment).

Usually in the form of special assessments or ever rising dues/property taxes.

I own my own business/LLC and am open to changing that structure for tax purposes, such as putting it under an S- or C-Corp if it would help with this situation.)I appreciate any and all thoughts on this matter as I can't seem to get out of my own head on this!

Prorated taxes (I understand this part)what other items that i should see on my closing bill?

For our customers, they fall under our business license and tax.

So many nuances from property taxes, insurances, what does airdna or rabbit say, cost of internet, HOA, permit costs, local utilities, are you doing maintenance or is someone else.... 

And similarly, if the applications reveal liabilities, you can simply give notice on the m2m.