It can look good on paper but reality is another story. 

I love real estate and am devouring anything I can find on the subject of investing.

Ideally, I would love to buy a multi-family property and rent it out, I would consider house hacking but I mainly want to my first property to be one that I can improve on and have it generate income for me.

your loan officer is nuts.you can have multiple lots/parcels on one deed..

Depending on how much liquid cash you have, you could also invest too on the side if you are looking to scale rather quickly. 

We are already surrounded on three sides by urban zoned homes.My neighbors and I have been approached by two individuals, one is a neighbor who is a real estate agent, and the other one a friend of a neighbor, who works with a real estate attorney; both individuals asked us to join them in working with the 5-6 developers they have approached.

I see a lot of posts on Bigger Pockets asking if I should refinance because my closing costs are XYZ.

welcome @Cam Caraher and congrats on joining BP, this place is the start for many, sure was for me longer ago than I care to admit.I'm not personally in your market, although was born in dorchester and grew up in NH, but this is a great place to meet locals.If you have not already a great starting point is the Meetups posted here, just search for your area and see if any meetups are happening. 

I think it depends on the problem.

on market deals in general will not be distressed enough.2. a good BRRRR isn't going to cash flow.so - are you looking at off market deals?