If not help me to understand why.  

Understanding the different policies and your risk exposure is properly the most important thing to understand.Understand your deductibles and what is covered with your specific policy (i.e, is sewer back up included, flooding)You can always get an umbrella policy if you want some additional insurance.

Hi all,I've purchased properties subject to, and I understand how it works.I am currently looking at a deal where the sales price is $290K and there is an existing loan for $150K.

There is slightly less risk if these MIL and additions have been done decades ago, versus last year, but still worth checking with the building department and zoning to understand what their enforcement is.

I understand there are pros and cons to all shapes and sizes of brokers, but I think I have concluded that I would like to go with a small brokerage in the Worcester area.

My understanding is most HOAs don't allow STRs which is why a lot of people have shifted to MTRs.

While I understand your frustration, it really was not economically sensible to expect a different result.

I would def get a mentor or talk to a realtor to understand what I am saying.. hate for you to lose money you put into the home..

There's no quick strategy, it takes time to build a solid wholesaling business.

Congrats, looks like a solid deal!