@Ray Reed
I recently purchased an 8 unit property where all of the units were well below market rent. Luckily, 2 units were vacant, and I was able to do some value add to bring those current with the market which gave me ample cash flow after 2 months. I do have several tenants that are elderly, have lived in this building literally as long as I have been alive, but pay below market rent. I was very honest with them and had a conversation with them. I asked what they could comfortably afford, and we came to an agreement. My goal is not to squeeze every penny out of a property if it means alienating an elderly 30+ year tenant. Other units are getting necessary increases, theirs will get the necessary but not ideal increases until the unit inevitably becomes available.
If I was in a situation where I was negative instead of neutral or modestly positive, it would be a more difficult decision. Having the number of units that I do, I would allow a building to run a modest, temporary deficit given my portfolio could support that one property in order not to relocate a long term, reliable tenant in the final act of their lives.
My advice, look at your own situation and work every angle of the problem. More often than not, a reasonable solution will present itself. With my own example, I cash flow on that property, but I don’t get nearly the returns that I could get were I to maximize increases. I’d rather have gradual but consistent increases, reduced turnover costs, etc. In the end, my view is that these people are essentially paying for my property regardless.