If you have units to remodel and are updating you can offer the senior tenant to move to the nicer unit and raise the rent, you can incrementally raise the rent, or maybe you can rent the other two for above market to make of the cost of the senior rent.

I also own a company with my brother, I Gotta Guy KC that does handyman and remodel work. 

It amazes me how much random transient travel it gets(bowling tournaments, pawn shop remodels, manufacturing employees, traveling photographers, etc). 

I am thinking of doing some remodelling inside, moving around a few walls, opening up the kitchen. 

Hey @Aaron Gordon congratulations on getting started on your real estate journey here in RI.Starting off with a live-in remodel is definitely a way to fast track your real estate experience.

We recently bought a duplex and are almost done remodeling it to get us to where rents need to be for that A or B class tenant.I personally find that due to long term buy & hold in this area, it’s just enough to break even for first year or two.  

Here is a list of Construction, Rehabbing & Generic PM softwares that may be a good solution:Construction, Remodeling & House Flipping Specific PM Softwares BuilderTrend/Co-Construct - Home building project management software specifically built for custom home builders.

Remodeled all the units and brought gross income from $30k to $43,500.

Btw, about the need for rehab, I'm talking about what I think should be fairly straightforward things, like replacing carpeting, repairing drywall, but not a complete gutting and remodeling.

I would say a complete home remodel definitely has challenges.