I am the co-founder of a vacation rental business, we use google trends to help us decide what city to target through advertising and how busy that particular city is during their peak season.There are small mountain cities in Colorado like Telluride that stay pretty relevant all year round.

A few of the trending threads on BP have been super entertaining.

I would expect some kind of project management fee for something like a roofing project or other improvements that are outside of normal maintenance calls.The PM is an important person in your team.. talk to a lot of people and find what seems to be the trend for the area and find the balance of price and what your expectations are.

On page 10 they have a graph of "Apartment Cap Rate Trends" compared to the 10 yr treasury from 1990-2016.

I included an itemized list of all the renovations, I also included current housing market data to show the appreciation trend in that area.  

As a general rule, if property taxes are high in a city/town now, and they have a looming pension crisis coming in the future (many do), the trend is not in your/our favor.I admit that I don't have a lot of Massachusetts experience/exposure however, so it may be that the price point and lower assessed value more than makes up for any higher tax rate.

I need to work on the economic analysis of the place I want to move to, to determine the possible long term trends.

Find a investment property contractor and RE agent ( not to sound sexist but a women with experince working with investors, an eye on home trends and staging skills) to partner with.

Makes bookkeeping better, keep track of thoughts, see trends, etc.

It will be interesting to see the migration trends within the US over the next 5 years and how it compares to the last 5 years.