Yes, Yes and Yes. prices are relative to the market and the area, you happen to be looking in a very high priced market where more things are demanded. i'm sure you may find a diamond in the rough somewhere, but to start off you may want to start looking in a different class neighborhood, a little lower but not as expensive.

My personal favorite is the Black Diamond meeting in Waltham (alternates every month with their Worcester location, next Waltham one is May), it is worth the drive.  

My favorite is the Black Diamond meeting that alternates every other month between their Waltham and Worcester locations so you are in a decent area to go to both, this month is in Waltham.  

Sorry to be so blunt and weary, but I work with bank REO's and they have limited inventory and you happen to find two so called diamonds in the rough and pass them up or and mention there still available.

Start with a competent broker, someone who can see a diamond in the rough and know that your end game is to buy and sell.

I target C- to B- areas, and look for the Diamond in the rough, an opportunity that I can force equity via rehabbing, then lift and improve the rents in areas near to Down Town on cities that are growing.Buy small at first, i.e.

This Homewood diamond in the rough was purchased for $105k, renovated for $40k, and resold for $195.

We buy  our plank from Rite Rug, Diamond Flooring and Sherwin Williams.  

Both I cap rate and earrings on downpayment!

Probably the closest one for you would be the Black Diamond meeting in Worcester (2nd location in Waltham that I'd recommend going to in addition to the Worcester one).