The reason being is that I have two years of a local community college ahead of me and after those two years I will be moving to California to finish off my degree which means I wouldn't be able to take care of any rental properties in NJ (where I live now).

I have agents that work under my brokerage, all with varying degrees of experience.

I know this hurts my cash flow to a degree but my strategy is to buy and hold for the long term so it makes sense for me.

Based on that combination of factors, you appear to be thinking what I'm thinking, this guy has substantial untaxed income.Yeah, the HOA has insurance and there actions to date suggest they know they may be on the hook to some degree because their guy so strongly recommended him to us.

My father is a building contractor, I do carpentry full time and also have an associates degree in Building Construction Technology.

Really it comes down to what interests you, resources, model, risk tolerance, neighborhood, and degrees of active versus passive.

My real estate includes my personal residents which I purchased in November 2016 for $130,000 and house hack to a certain degree with one roommate living with me.I also own a 4 bdrm college rental in a nearby market that brings in $1540 a month but due to taking an equity loan out, I only net roughly $250 a month. 

We get lots of people from Wisconsin here all winter long when it is 80 degrees out.

As for pursuing a nursing degree i am decided for it already despite the increased taxes and liability.

It's worth the money.Don't forget, just because someone has a law degree doesn't mean they know anything about your particular interest.