Do you have a relationship with a local lender that would be more willing to work with you now & in the future vs. a larger institution to whom you're just a number and they don't really care about at all.

I bought a time share in the Berkshires (MA) back in 2014, I never use it (I prefer airbnb) and now I'm stuck paying the maintenance fees. 

Hello Shane,The market is for real.The demand is high and a home is better then an institution.  

@Jason Ma.

I am in the process of having a tenant move out of one of my 2 families in Eastern Massachusetts. 

I did in Western MA and found that even though the gas furnace would be more efficient, it cost more up front and there were few propane service providers in the area. 

Thanks guys, im gonna buy a duplex cause I feel like it only make sense, mainly because im from MA where its just as much to rent an apt as having a mortgage, but I do realize that a mortgage comes with more and I have some money saved and a partner.

Then refinance through a different institution or union to draw the equity and pay off the HML.

@Jason Ma you should start with the local realtors in the market you want to look at.

Try to go to more than one institution and get numbers and data on what they can do for you.