Typically the adjoining property owners will fight you especially if its single family residential, but you need to prepare a solid presentation to the Town that your plans are the best use for the property and more specifically monetarily for the Town and its residents.  

I have a solid portfolio of singles, duplexes and even my first 11-Unit picked up this year. 

In my area of the country every single person has a real estate license.

I've invested in/renovated a number of single family properties in the suburbs of Philadelphia (Mainline), with values ranging from $400k-$1.3m and decided to tackle a significantly larger project 6 months ago; comps were incredible with high sale prices and very low days-on-market, it looked like a home run.The loan is under an LLC but with a personal guarantee; the renovations are complete and the house is beautiful, but the market has been unbelievably slow compared to the previous 3 years, on which our financials were based. 

One is a duplex (which is the first in a long time) and the other two are single family homes.

If this is a single family...you should have 1 month vacant every 3 years or so.Your interest seems low, but maybe thats because you are paying points.

Hello Caleb,The default tax entity classification for a single-member LLC (SMLLC) is a "disregarded entity". 

I’d say stick with single family but he’s made small multi work well for him. 

In residential language, I would explain my plan as building a single zero lot line home while setting groundwork to later build the second.

I always suggest young individuals who want to get into it , have to live in the city, and only have the cap to put 3-5% down, to buy a condo or even better single family house and rent out the rooms to friends or even potentially AirBnB, if you have the single family house.