If its a log cabin it might have trouble qualifying for the refi - would be smart to get some opinions early if that is your gameplan - would likely be a bigger potential hurdle than the gift/original purchase process

I would like to invest here but there are two large hurdles: Negative cashflow down paymentI feel that Boston is a fantastic city to invest in.....if you are well capitalized.

As for short-term financing, they are fairly easy to work with but the biggest hurdle is their internal credit model.

Biggest hurdle right now is finding a reasonable cleaner.

My next hurdle to tackle is gas/water.  

So the enforcing agency gets to determine, but HCD is present to intervene if the enforcement agency is being unreasonable.  

Obviously anything can be negotiated or it depends on what you agreed upon, but what do peers in the industry consider acceptable for this and whats considered unreasonable... 

It sounds like you are going to be a tire kicker wasting your time and your agents time with unreasonable expectations.

I get what your aim is and I don't think it's unreasonable.

It is unreasonable to think that you will have positive cash flow if you are borrowing 80 percent.