Then, when they enroll in the local schools, I had to sign an affidavit certifying they are tenants, on the lease, and furthermore I'm responsible for fines, and reimburse the town for money spent on educating an illegal resident.

Since this is your primary residence there are no taxes on the sale up to 250K I believe.

I'm from Laredo, Texas, but my family and I are currently living in South America and will be residing outside of the U.S. for the next 3+ years.

We were ok not cash flowing because we knew we were in an A class neighborhood and the profits would come from appreciation. 2.5 years after the acquisition, we sold the building and realized a 22% appreciation (definitely atypical results)In my opinion, if you're going to reside in the building, buy a 2-4plex in a neighborhood where you want to live and the appreciation will come. 

Resident Demographics. 

You qualify for the exclusion now (residing in it 2 of the last 5 years), But you will get a prorata share of the exclusion either way.

Please note I've done some research on these markets (I'm focusing more on the western side of the state), this is just my knowledge/experience as a long-time CT resident. 

Idk if I can use that multI as a secondary residence and live in that ?

Account Closed - Are you talking about a house to reside in without any renters?

I'm currently an orthopedic surgery resident (year 3 of 5) and have had an interest in the small business world and real estate as long as I can remember.