It's been rented for a year and a half and needs repainted.

Really dirty place and that scared my wife, but I wasn't too worried about it as it's mostly cosmetics and we can get the place cleaned whenever they leave.The goal with this first one is to sit on the cash flow, save up it up for 7-10 months and repaint the outside of the duplex.

The manager offered to repaint one of the rooms during a turnover and we told him he didn't owe any rent that month.

In 2018, the HOA issued a violation and informed us, we need to repaint the entire exterior of the house.  

Nice and easy to deal with leaks, issues, repaint, etc.

., they might balk at repainting it, if they do repaint it they might do a crappy job/use inferior paint/overspill etc.Sure you can have a contract, but try and collect on that after you part ways.A step down from my hard "no" would be take a deposit equal to paying a contractor labor/materials to repaint the unit. 

Even at that point you will have a "used house" meaning that you will have to repaint and all your new appliances and flooring will be slightly worn so you will be selling a "used" home like other owner occupants vs fully renovated and "new to the user" home that you are currently selling.

Some 409 might scrub that closet door dirt and save you The price of a repaint on that tan closet door.Look, if you're gonna be in this business saving a couple of Bucks here and there kind of adds up especially since your new renters will probably dirty that place up in about in about four months anyway. 409 also Works for little kids crayon marks sometimes too.Good Luck!

This includes learning how to be a landlord (how to market, local laws, setting up communication and payment systems, setting up leases, setting up a bookkeeping system), maintenance/turnover (how long it takes to repaint, get contractors started etc.), understanding how much quality work costs, and also mistakes you make. 

Spreading bark mulch, updating smoke/CO alarms, making sure the water heater has two straps, and repainting front doors.