I flipped and did some buy and hold when I lived in Florida.   

I live in Boston, but I was advised to start my real estate business elsewhere as Boston is very competitive.

basically if anyone has any tips when it comes to researching plots of land in order to make the right purchase i would greatly appreciate it get with a realtor. we underwrite land at no more than 10% of after built value. in our market we build under the average new build value which is about 515k. we like to be around 420-450k and smaller footprint about 1500 sq ft with attached garages. we build close to urban core where everyone wants to live and net migrations match up. but suburban is fine. if you give more context I can help but in most markets land is a buyers market. most people aren't looking at it or buying it. 

A 1/1 with a 4/2 on top is perfect for the hacker to live in the 1/1 and cash flow on the higher rents.2.

I could see a requirement, perhaps under the Patriot Act, that requires all landlords to get a SSN/TIN from everyone living in a unit and report that (or lack of) to the federal government.

Additionally, you may wish to speak with a CPA as to whether or not becoming an S Corp is the right decision – they can assist with reducing self-employment taxes.

Another option is house hacking—buying a small multi-unit, living in one, and renting the rest to cut costs.

The reason to have comparables is if you are representing someone or perhaps purchasing a house for yourself to live in.

If you plan to live there in the winters, you might have a hard time doing long term rental outside of that and finding a new tenant every summer.

I own a 4plex where I live in one and rent the other 3.