Fourth, the real estate taxes accumulate. 

Start spending time submerging yourself within real estate and your confidence will accumulate. 

My question is it more benificial to save up more money to pay for a second home and accumulate more debt or pay off this first one asap?

My goal is to house hack consecutive years to accumulate units with relatively low money into the deal.

I’ve never met someone who credited the accumulation of their wealth to diversification.

Over the last 30 years my dad has accumulated a net worth of somewhere around 20-40 million  by investing in gas station properties, operating the business, adding value by building cash flow, and refinancing / sell to pull equity out, and repeathe helped me get started in the business by helping buy my first gas station property and businesses in 2018.

. - Married with a 15 month old daughterI am looking to accumulate wealth over the course of several years by leveraging my retirement savings.  

I was able to perform significant renovations, doing a lot of the work myself and my partner - accumulating some sweat equity.

Or do you set up a cut off, for example you end up accumulating $10K from expenses mention above, and you stop including these expenses in your NOI calculation until you have to dip into the $10K reserve you built up.

You are likely listening to podcasts of people who would love to be in your position.It ultimately depends on what your position in life is and what your goals are.If your current cash-flow can sustain your current life-style, there is no reason to go crazy over risking capital for extra money that you don't need.The goal is to enjoy life not to accumulate extra dollars.Best of luck!