I’ll try to keep this as short as I can but also paint the exact picture that I am in and desperately need some advice.

The biggest issue I find with renting something at over market value and getting someone desperate and willing to pay the high rent, is they will always be looking for something cheaper and you might have a lot of turnover. 

I think the due diligence fee falls squarely in the category of "stuff buyers do in a HOT market when they desperately want a deal and simply don't know any better!"

They do this either by lying about the true value of the property or by finding sellers who are so desperate to get out of a bad situation that they'll take a bad offer just to put out whatever fire is going on around them.For the record, Mass law is crystal clear. 

If you're looking to use your house as collateral I think HELOCs are definitely a better option than cash out refis as long as you aren't in desperate need of immediate cash. 

We are a little desperate and don't know even where to begin.

Grant, the PM’s here are desperate.

If all else is equal (same offer price and contingencies), the love letter may make or break the deal for some desperate buyers. 

You may get a desperate seller to agree to something, but you are setting your reputation with 2 realtors.

Not only are you being legally fair but these are screen outs for those whose income or credit histories do not meet your criteria but are still desperate for a rental.