So, without knowing yourself how to evaluate rehab numbers, you are stuck taking a gamble of investing some capital to perform some due diligence prior to making your offer to see if this is a good fit or not.

this is an age old question on BP..you have the Cash flow is the only thing crowd and appreciation is gambling .. and then you have those who invested in markets that historically appreciate who have gotten majorly rich over the last 7 to 10 years on appreciation with no cash flow to speak of.  

You like gambling, don't you? 

There are also investors that knowingly do this, gambling they won't be caught.PARTNERS (girlfriend): if at all possible, avoid buying a property with partners and having anyone else on the mortgage with you.

@Patrick Bergeron Hopefully you guys have an out and didn't gamble on the appraisal since you don't have enough funds. 

To truly be competitive and efficient, we need to take a look at our business taxes, sports gambling, and business regulations.This is a good start.

I have definitely heard stories of that being done and resulting in success, but in my opinion the risk factor is very high, and gambling on a potentially very sour situation with a "previously content but quickly turned unhappy" tenant, especially in Massachusetts, being such a tenant friendly state.

Its called investing , its a gamble , there is risk , and there can be reward .

You might need to look at that as "gambling money" rather than "grocery money" as it could be tough to enforce before probate is complete (or even after...). 

If your investment is cash flow negative it is not an investment and instead a gamble