Raise the rent on learning delayed tenant? What would you do?

[Gwen Fyfe]

I have a little situation I've been thinking about, and I wondered what the BiggerPockets community thinks.

I recently purchased a quad for my first house-hack, and it's going great. The previous owners were really good landlords and I have had zero problems with my inherited tenants. They're all really nice guys who live quietly and pay their rent on time.

One of them has been living there for upwards of twenty years. He's a good guy, bit of a hippie (so am I), and a little slow (which some would say is also true of me, ha!) I don't know the extent, and maybe I'm making some impolite assumptions, but from talking to him I think he's a little delayed. Independent, obviously, but living in this little efficiency apartment for 20 years and his mom's name is on his checks, that kind of thing.

He also hasn't had a rent increase in five years. His unit is currently sitting at $375, while the other two identical units which have turned over more frequently are renting for $400 and $425. And those prices are already a little below market.

I was planning to raise his rent a little bit, probably to $400. I discussed this with my grandma (my real estate idol and badass matriarch - don't mess with the 90 year old self-managing 5 condos) and she is of the opinion that I should leave the rent where it is as an act of charity. Self-imposed rent control. Because I'm already breaking even on my housing, and my tenant's income isn't likely to change, so that's $25 that wouldn't make much difference to me but may easily be a hardship for him. A big part of my motivation for getting into real estate is using my own lucky position to improve housing equality, so why not start here, right?

In my shoes, what would you do? Where's the balance?