Here's some background that might be helpful: My mom died last year unexpectedly. She managed the real estate properties that my parents hold. My Dad has been investing in real estate since he was 21, but he has been more operational/capital investments side. My dad and I are now co-managing, and I'm the legal and financial side. Yay, I'm a lawyer so I figured. We haven't had a chance to grieve because we have to get the financials straightened out, cut expenses, scramble to fund and save capital repairs, and manage her estate (properties weren't in that). This will take is going to take a few months to start to breathe. We are definitely going to change the way the business was being managed.

So here's my question: what's the best way to change the rent given our situation (Below)?

One of the main changes that shocked us both is how low the rent was on some of the properties. For the market it's probably 50-60% or more below market for 2 bedroom brick duplexes, for example. 

We've got to raise it, but we don't want alot of moveouts all at once, have to make a lot of repairs to rent given some of the capital demands we've just had (more surprises), so we're going to evaluate the properties and to check on those factors. It will affect alot of very long term tenants - 10+ years. Many of which are on a fixed income, and Dad is concerned about people moving in the winter when it's cold. Most are now on automatic renewal MTM leases. We've batted around ideas by raising gradually - in two parts, 1 soon and 1 6-9 months later, and letting them know that and starting with increases soon on some people and in March on others. Some people we're likely going to pull the bandaid on because we feel good about not having to do much to re-rent it. We're doing that analysis right now.

Sorry this post was so long.