How far below market do you keep a good long term tenant's rent?

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I have kept rent very low on one of my units because it needed work. I'm getting work done now and would like to bring it closer to market. I'd love feedback on the following:

Tenant has been great for 15 years. His rent is now $270 below what nearly identical units are paying. In this area, same square footage, amenities, etc. is upward of $1900/month.

Is $270 too big a gap? If so, how much would you raise? Would you increase one increment, or over time?

[Kevin C.]

If I wanted to keep the tenant, I'd spread it out over at least 3 years, if I didn't care if they moved or not, 2 years, if I rather they moved anyway - all at once.

Personally, for a long term tenant that has been easy to deal with, and has taken care of the house, I'm OK with rent sliding below market over time.

I have a tenant now that is in her 4th year, and last year was the first time I raised her rent.  She keeps the house immaculate and has never been a bother.   She's at least $150 under market, maybe $250, but I'm OK with it because she has been such a super tenant.  She is set to increase again next year, about 3%, but she'll still be under market.

When she moves I'll bring the place up to market, but until then, I'll enjoy no vacancies, a well kept house and a model tenant.  For a tenant of that caliber, being a little under market is fine by me - we both win.