I think as far the numbers are concerned (assuming the right investments), it becomes somewhat of a wash, although my numbers could be very wrong. 

I started pressure washing roofs on the weekends to make extra cash to pay off credit card debt.

I get how fresh paint, a power wash can go a long way, but most of what I've seen need more than that.

First I have to get rid of my AWEFUL inherited tenant.

Wash, Rinse, Repeat

I watched in awe as people reportedly got rich during the boom. 

GEEEESH I THOUGHT I WAS THE AMATEUR HERE TO LEARN BUT YOU GUYS SOUND OLD AND WASHED UP LIKE YOU STOPPED YOUR EDUCATION. 

Plus, when you do eventually sell, barring some truly awe-inspiring gentrification, you're stuck selling to another investor who is going to try to get the best deal possible, just like you did.

I'm curious how they handle the holdover rent; my guess is that they'll try to wash their hands and leave it to you to pursue from the guest/tenant.

Pressure wash surfaces that may be slippery.