Quote from @Laura Yelin: Hello BP'sI like Sherman...I lived there for about 3 years many years ago and still sell and rent there.It's a slow wealth building market in my opinion, not get rich quick.Mostly blue collar stable town.

Those that own it can be harder to sell as the cash flow from the business will cover the debt service for the business, but not for the real estate.Example: I had a very high-end assisted living facility on the market. 

If not, you’ll need to resolve these liens, which could complicate the investment.Current Occupants: The family living in the property could be protected under Massachusetts’ tenant and housing laws.

I'm still flipping but I do live ins so only 1 every couple years, mostly San Jose.

I previously lived in this property and never locked myself out of my room so I never looked nor do I even know if I have a key for the bedroom door.

Your primary residence - if you've lived in it for 2 out of the 5 years prior to selling you'll get the $250K/$500K tax free iike @Clint Galliano said. 

For the son to qualify for the $250k exclusion, I believe he would most likely need to meet the ownership and use test, meaning he needs to own and live in the home as his primary residence for at least two of the last five years before the sale.

I renovated the home while 3 of my friends lived with me and paid my mortgage.

If you need the cash flow to live on and it will improve your lifestyle, then go for it.

(For context, it's a 2700 sf 4 bd 3 bath house in an upscale Northern California suburb.)Kitchen A: Traditional, features a 48 in fridge, 36 in cooktop, window sink (no view), pantry.Kitchen B: Designer, features a 60 in fridge, 48 in range, large kitchen window (no view), sink facing living/dining room; unfortunately no pantryKitchen C: A Little Bit of Both, features a 48 in fridge, 48 in range, sink facing living/dining room, pantry, unfortunately there's no window.Total countertop space is roughly the same (22 ft)  in all three layouts.