New floors (Lifeproof series from Home Depot), new water heater, new paint on everything, interior and exterior caulking as needed to reduce air flow, some exterior paint on our section (shhhhh, don't tell the HOA) What was the outcome?

My current mortgage is $830/month with total expenses (HOA, garbage/sewer, insurance) totaling $1,049/month. 

Holding cost for Taxes, HOA, and keeping grass cut are about $1750 per year.  

Its hard to rent the house because its a gated community with strict roles and HOA, and its easier  for me to just rent it out to family.

Meaning you want to ensure that the rents will cover 125% of the PITI + HOA on the property. 

The HOA and the property management fee's I think are too high at a place I'm looking at.

I'm seeing that my HOA may have some restrictions on renting out rooms.

Then they pay off the lender, property taxes, insurance, HOA and then finally you. 

I bought a townhouse back in 2015 (part of a 8 property complex) and there was no HOA noted in our closing docs/due diligence.

Current mortgage all in(including HOA) is around 1k/month and looking to rent for 16-1700/month.