Just closed on a condo and inherited a tenant who is there on a month to month lease. She has been a tenant for a couple years and is very clean and always pays on time.
It is in our strategy to raise the rent a couple hundred dollars at the start of the new year.
What would be the best way to go about doing this as to not upset the tenant too much?
She's going to be upset if her rent goes up several hundred dollars regardless of how you do it. The only thing I can suggest to less the blow is to see if there is anything that needs to be done in the unit, either repairs or small renos, and do a few improvements which will get you more rent down the road.
Also you might not want to wait till the first of the year. If the tenant decides to leave you would have a much easier time filling your unit now, rather than in the middle of winter.
I would raise them $50 immediately (since she's month to month) on a new 12 month lease.
If she balks and leaves, then you can get a new tenant at market rate (assuming the market supports a couple of hundred dollar rent increase).
If she stays, then another $50/mo next year, until you're at the number you want.
It'll take more time to get where you want it, but a good, clean tenant is INVALUABLE.