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?

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.

You had the vents "cleaned" but does that mean someone vacuumed them out or someone washed them?

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).

The main issues i see with this idea are:1) Splitting utilities is going to be very expensive and most likely kill any real margin 2) Actually get permission to split the home, there are however seperate entrances and windows so there might be hope.Any Input?

The main assumption is that both you and the seller can read and understand the sales contract you will be using...and it should be readily understandable.