It is stated on the main lease agreement in print that room rentals are not allowed unless agreed upon by the landlord in writing.

Ok, The amount is high, but things like this are so it's not my main concern.  

I recently joined BP to get started in REI with my main interest being rentals in the Massachusetts area.

Mainly, the systems implemented are fascinating (VA, automated offers, etc.)

My main focus has been buy and holds but I’m not opposed to a flip if the numbers are right!

That way you can make a quick trip to the property whenever needed and spend no more than 4-5 hours traveling back and forth on a single day.For Bay Area Investors, that basically leaves you with Sacramento and Stockton for driving distance (there are other options, but that's where you'll generally see the best returns) and either Las Vegas or Phoenix Metro for flying (less than 2 hours).Wherever you decide to invest, here's the two main things you're going to need:1) Knowledge of the Market: Just google "(name of area) real estate" and read every single news article on it from the last 3 years.

Because the purchase price is pretty far under market value, will that attract attention from the IRS, or should I be fine?

However all of the attraction of investors, plus a new mayor who seems to be up for the task, those rough areas are slowly being turned back over.Feel free to holler at me if you are thinking about coming in town. 

Branding isn't my main focus.

I just completed the inspection yesterday and it seems the roof will need to be fixed(over 20 years, the boiler system is very old(there are 3 boilers), one of the 3 hot water heaters(HWH) is leaking and the 3 car garage (which is one of the main reasons the property is compelling as an investment purchase) is not structurally sound and may need to be demolished.