Water damage never happens in small amounts, until its noticed and by that point it's typically a larger job than $1200. 

This tenant has since had another child and moved to a different larger unit of mine and is still one of my favorite tenants.

I highly suggest against that and just doing one larger rent increase to $1000, but if you are only trying to do one unit at a time, make sure you don't try to make a drastic increase to all 4 tenants if you can't afford for all 4 of them to be out at once.I'd consider showing them some data on comparable rentals and let them know you are trying to improve the building by renovating the units.

A mid-term rental near a major hospital could bring in $1,800–$2,200/month, covering a larger part of your mortgage than a long-term rental. 2.

A property manager handles the day-to-day tasks, freeing up your time to focus on other areas of your life or business.

@Kyle Peters, I personally estimate 2 things per task to generate 3 estimates!

@Cody Holt I would sell and take the proceeds and buy larger properties that are multifamily.

Do you have a full-time job already, assuming you have extra time, do you want to spend it doing another brain-draining task or would you rather spend it enjoying yourself?

Larger Syndications: When you see the syndicators achieving the larger raises that can attract the checks written by the private equity/family offices but are instead raising those funds in smaller friends and family check sizes, that would give me immediate pause.

Ideally, we’d like to sell both of the rentals, and use the cash to place a down payment on a larger multi family home investment property, maybe valued somewhere around 400-600k.