I think I may have been putting the horse before the carriage with my idea about jumping into flipping houses first.

Here are the details-Multi-family, 2 separate homes, front house and carriage in the back, 2 BR 1BA each.

(To the best of my knowledge, less than 10 buildings are zoned for it)Also STR in carriage homes and basement suites became illegal so .....Don’t make your investment plans based on STR unless you are in a “C9” zone. 

Hopefully that will put you in the right headspace to start making changes to your situation.Then when you're ready to make some moves, I would suggest you to buy a primary residence to house hack. 2-4 units or something with a mother in law unit or carriage house.

Targeted buyers are primarily those who do not want to be bothered by external maintenance typically associated with home ownership, sometimes because they only live in the patio home for part of the year.[1]There is not usually a legal definition of a patio home, and some houses called patio homes may alternatively be marketed as townhouses, garden homes, twin homes,[2] or carriage homes[3].

For instance, windows on the first floor -- I've heard that intalling replacement windows on FIRST floor is biggest bang for buck due to hot air rising ... also, the basement in my 7 unit is an old carriage house and is 10-11 feet high!

It is VERY deferred and has a carriage house in the back.

There were also a very old chestnut and a butternut  standing by the carriage house.There is an ~5' x 10' section of stone in the east gable which needs repointed and a couple of loose stones moved back into place.  

Now there is back carriage house that is about 600 square feet with 1 bedroom and 1 bathroom. 

I've been airbnbing my carriage house attached to our house - its a studio and simple and has done very well.