@Dana Powell  I see they are already painted radiators of course you have to repaint. 

You are adding an extra expense every 5 yrs to repaint.

Put new PEX supply lines in, repainted everything, rebuilt some windows and repaired others.

I added more cabinets in the kitchenI added a handrail to steps in the rearI had new cement poured on sidewalk, porch and drivewayI added new storm doors to all 3 doorsI added new cordless, faux wood blinds throughout home (Home Depot installed)I repainted and repaired detached garage Lessons learned?

Some drywall replacement, repainting, need to add a backsplash to the kitchen, maybe replace cabinets, flooring could be redone.

I added more cabinets in the kitchenI added a handrail to steps in the rearI had new cement poured on sidewalk, porch and drivewayI added new storm doors to all 3 doorsI added new cordless, faux wood blinds throughout homeI repainted and repaired detached garage Lessons learned?

You haven't repainted an entire unit in 14 years? 

I’m planning to update and repaint, maybe increase rent on one side to 3000-3100 while I live in another unit and replenish to legalize garage space.Monthly payment: $7033. landlord pays for water, everything else is separate.It just feels very tight in the beginning before getting ADU gets legalized. 

We're planning to upgrade a large kitchen (repainting cabinets, new hardware, and new countertops).

How are you going to have so much appreciation from repairing a water line, replacing one or two appliances and repainting one room?