Being a landlord in Boston will expose you to interesting challenges that will frequently change over the course of many years. In many cases, it can seem as if Massachusetts law is stacked against you, especially when it comes to dealing with difficult tenants. We all know that the courts in Boston tend to favor tenants even when the landlord is clearly the harmed party in most cases. No one really knows how or why this slow slippery slope of heavily siding with the tenant began. Nearly every landlord in the Greater Boston area says that there are massive differences in the way landlords are now treated by the court system and politicians now than even twenty years ago.
Property owners in Boston need to be far more diligent in their process of apartment leasing. It is abundantly clear that it is more important than ever to pick and retain the best tenants upfront so you don’t end up in a financially harmed position.
To be clear, most tenants are respectful and honor the lease in a fair and reasonable manner.
There are usually only a few bad actors that cause landlords endless headaches and financial distress. That being said, when you get a god tenant, you must do everything in your power to retain them. Having longer-term tenants cuts down on the wear and tear of moving people in and out which is usually when a lot of damage occurs. For the most part, less turnover saves a landlord more money than constantly turning over tenants. Most landlords in Boston prefer that their tenants stay for multiple lease renewals as it significantly cuts down on additional paperwork and related security deposit work.
If you want more of your reliable tenants to stick around after their lease is up, then you need to know how to keep them happy. Here’s how you can do just that:

1. Communication
Whether it’s sending out a monthly newsletter, dropping a note in the mailbox, or even sending out a mass text, it’s important your tenants know what’s occurring, especially if…