Unfortunately, the cost of entry into the Boston market, plus it being hot are two strong negatives (at least in my mind). 

If you have not flipped before, they usually want to see some sort of experience before lending you money.Stay with your day job, and rehab on the side. 

Flipping a house , money is lost because the investor , usually paid too much for the property and second , they way underestimate the rehab costs .  

So high risk places usually have higher returns)

For example, water heater install and there is no shut-off valve before the heater it cost $150 for a $20 part with 15 min of install.The challenge with doing a project (one that involves more than one trade-like kitchen or bathroom update) is there are usually holes in between what each contractor does and filling those holes is challenging.

Due to student loans and mortgages on 3 properties, even with significant equity I have a VERY negative net worth.

Honestly I will be happy as long as the house pays for itself. and doesn't negative cash flow.

Usually they (condo associations) are running to get those past fees.

Paying off a loan is usually not the majority of the payments to own a home, so why do it?

@Evan Ventura,People here on BP have also successfully used the cheap IKEA countertops (around $75-99 for a piece). at that price they where treated as expendables (one per tenant), and some even reported getting the install time with demo at 2-4 hours.for the other, you need to "waterproof" the common points of water entry:-caulk between the wall and countertop-use varnish on points contacting sink-use good glue near the oven/range since the usual pressure-activated glue does not fare well with heat