I'm looking to purchase a 3-unit property in Massachusetts.

You need an assemly line approach, which is repeatable.Work the math backwards, determine how many units you need and what type of debt service they can carry for the deisred cash flow.

I am searching into multi-family properties, moving into one unit and renting out the others, then eventually moving out and renting out all units.

Some will do it with a 2-4 unit property, some will do it with a SFH with an ADU, and some will just rent out the rooms. 

I am definitely being ultra-conservative when it comes to repair and maintenance costs but still the 2-unit multifamilies do not seem to have a good cash flow. 

The unit is in downtown San Jose and rents for around 2K.

I've had a couple of people suggest to me to 1031 exchange my SFH here to buy multi-unit OOS or many SFHs...sounds like huge headache venturing into the unknown and all those tenants, repairs, capital expenses etc. 

I am a mid level real estate investor with scaling pains and would like to know what Mastermind groups are out there for investors with 20+ units that are looking to grow to 500+ units.

First of all what is your thoughts on using the section 8 fair market rent number as the comps for what i can get for a unit , and secondly will section 8 care about a garage or the square footage of the unit ?

I need to renew my 52 unit in South Daytona Florida insurance very soon.