Investors know the contractor has to make a profit, and I like to work with contractors who are transparent and up front about what their profit margin and fee is - not someone who is trying to bake it into the cost and hide it from the investor or client. 

In 4 years they could've declared bankruptcy and had a fresh start.

I was broke, fresh out of college and found bigger pockets after deciding if I need to pay back student loans, or invest in real estate.  

She only lived there for 2.5 years, and the house was freshly painted before she move in.

New floors, fresh paint, all new kitchen and bathroom.

I figured I could get the place completely rehabbed for $30k and start fresh. 

This way you're giving them the improvements they want and you're giving them what feels to them as options/a say instead of simply telling them their rent is going to be higher.Sure - you may want to upgrade things they haven't mentioned - just bake some of that into the rent hike. 

I've also heard that fresh books was a good program for the non accountant so you may want to check out. 

Some HOAs bake all of that into monthly fees and others don't.  

Needs a fresh younger mind in there.