Once I partner with someone / raise the capital for a down payment, I feel I will have overcome a big hurdle in acquiring my first deal! 

The taxes are the main concern though.

I guess my main question though would be what other area's should I be looking at.

My main question is whether it makes more sense to rent out our current residence or sell it and use the equity to invest in multifamily?

Recently we got our permit to go forward with the duplex that has come with a few hurdles.

Thinking about this from a potential purchaser perspective, purchasing a property that has the main two levels metered separately from the basement could be a positive to someone with an investment mindset...but someone that just wants a vacation property and wants to use the whole property might find this annoying to have two separate bills.

One last hurdle to clear - rehab draw schedule 

My main gig is selling Telecommunication & IT equipment and services and would love to supplement my income with some real estate. 

There are definitely prime areas surrounding the main bar/restaurant districts that go fast. 

Hi, BPers....I am a Bostonian who is thinking about buying my first rental property in Maine...ideally buy and hold for VRBO (as I would want to use them off bookings as my own vacation home).