If you do that but look for a decent option, not a perfect retail type purchase, I'm willing to bet you can make a great step in the right direction. 

Making all the wrong choices when I was younger hasn't allowed me to break past the lower middle class.

If you buy in a location where prices and rents are increasing below the inflation rate, your income will be eroded over time by inflation, and you may have no choice but to decrease your standard of living over time.

In a year from now come August of 22, 1 of 2 choices will be made.

We might make different finish choices (cosmetic vs. durability) but the price is often similar.

First renters were horrible and decided to go with a Property Manager after that which was a great choice and made the property autonomous after that.

I bet it's changed a lot since then.

Ideally if I can find a property to add value to, that would be the best bet.

Adding new windows can add value to the home, if they are very old, then replacing is a good choice in most cases, not all. 2.

I wouldn't bet on any helpful changes in the near future.