What im suggesting is a bit Risky but does work if you have the stomach for it.

Ok, yes there are parties, and damage is a concern.However, you can put ALL of that in the lease AND add on up to 2 months security deposit.Meaning, if you can stomach the damage, it's worth it.

When I now go to my lower end rentals that I used to live in, I find it difficult to stomach moving back in other than the low cost of living compared to where I live now. 

If they are generating $3000 a month in cash-flow combined you can probably easily stomach most repairs, appliance replacement, a vacancy, etc. and not "feel" it.  

I want them out as soon as possible and am willing to stomach winter vacancy but with strict Massachusetts eviction laws (also they have a child) I want to execute at the right time and hopefully mitigate risk of legal fees/tenant living rent free.

(I doubt they would blame you if that happened.) 3) Make sure they know there is risk and make sure they can stomach losing their money.4) Thereby, don't ask for more than they would be comfortable losing.

Also, Seattle is currently too rich for my stomach.

Some do not have the stomach for this type of stuff & that's ok.

Panic that caused me to stay awake at night with a pit in my stomach feeling that something was wrong.

I am almost paralyzed looking at dozens of lenders and the thought of going through conventional financing again turns my stomach, lol.