There is money out there federal or state, county, etc.

Didn't I just see a proposal that would change STR classification so that they will have to pay 4x in property tax?

Here are a few key things to keep in mind:Understand the program: Section 8, also known as the Housing Choice Voucher Program, is a federal housing assistance program that helps low-income families, the elderly, and people with disabilities afford decent, safe, and sanitary housing.

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.

How can I avoid capital gains tax if at all?

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!