Up until now we have been using Evolve vacation rental to “manage” our properties and to cut a long story short, we are ready to take it on ourselves in order to scale our business.

Don't cut the corner on this one to save money.

I concur with Jay: it's all in the discount and $100k doesn't cut it.My 2 cents,Mike

That way since there is a connection to the basement there is not issue with you crashing down there.If you don't want to do something like that, I would cut the basement off from the first floor and just rent the first floor, leaving you the basement to crash in when you want.Or see about getting the basement made into it's own separate unit now that ADU are allowed in Mass (although the law may not kick in until the new year)Also your town may now require a certificate of occupancy to be issued before you can rent it out and they may have something to say about this basement connection anyway.Just my two cents as they say.

There are other things but this is the thing that creates the most waste of time. 

So never waste a failure, learn from the no's and how to attack similar conversations or situations differently in the future to give you a better chance at success.

@Jim Witten  I think his concern may be that he could get cut out of the deal if you don't sign a listing agreement with him.I probably wouldn't sign the agreement, but I would sign a letter saying I agree to pay him x% if his client buys my property.Regardless, I wouldn't let this opportunity slip by without checking it out first.

Total still owed $13,600 (rent, late fees, legal fees) and $550 for the locksmith.Place reeks of pot, she had her adult son, who by the paystubs left behind only made $152 a month and spent his days laying on the couch (which reeked of pot) smoking and playing x-box (abandoned and power supply cut up). 

Lawyer up--anything else is wasting time

Looking to sell my home, but it is very much a home that will sell itself, how can i be the one to sell it insted of wasting money on extra fees of going through a realtor?