Thanks for the insightful replies guys. I can raise the rents according to the lease agreements, but I have not yet raised rents on existing tenants, just as turnover occurs a little bit. I have a lot of tenants that have stuck around for a few years. I always thought I shouldn't raise rent on existing good tenants but my expenses are rising and they are staying...
I am a renter as well, and I almost expect a 10% increase after two years of renting here and would be ok with it. Maybe I am less sensitive bc I am in my 30's and not a student anymore, working full-time.
I think I will give them 3 months and phase it in so it is not such a shock as you suggest. Funny I thought I was doing them a favor by delaying the rent increase but now it just makes it a bit more uncomfortable for everyone. :(
Kwill I am a bit in between your two landlords, not quite as diligent as the one but I keep on top of maintenance, contracts, etc.
Cripzy I do try to keep them in good shape, but the apartments are old and that makes them a little more attractive to certain tenants I think--I try to maintain them without renovating too much to maintain their charm. I never have to advertise, they fill by word of mouth. (see pics)