@Michael DartenMichael,Let me know who choose and how it works out, I wouldn’t mind having a backup.

However, if both are desirable and available in your market, I would definitely choose smaller multifamily (1-4 units) hands down. 

Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

The answer to this will come down to comfort level, funds available, and strategy you are looking to implement. 

It’s all about what will draw guests in and make them choose your listing over others.2️⃣ Standout Amenities: Rentals that offer something extra, like a hot tub, game room, or eye-catching design, often attract more bookings and higher rates.

Choose my own real estate agent

Company is called Comfort Capital.

Do you have a lease I could look at, if you feel comfortable sharing. 

Your income needs to be 100x it and you need to invest 10% of your net(so less than $5mil) annually in structured product type investing incl RE, let it season for 3-5 years, re-invest the first bit of profits and by year 8-10 you should be comfortable.$500k annual income is alot for your average folk, but it's not "retire me" income at all.

With the cost of utilities and the level of comfort people feel is mandatory now there is no way I would want to be on the hook for it.