There is some fees to start like applying for your license , pay taxes, etc but it still seems worth it.  

If it's the former, still househack unless you're investing in one of the better growing areas that you anticipate large growth in and can view yourself as a speculator. 

My first issue is I live in a HCOL area (NY) and investing locally seems like numbers are not worth it.

Typical deal is to buy a property for $2-3 million, put $1-2 million into it, all in for $3-5 million, stabilized asset is worth $13-17 million.

Perhaps worth checking out.

Is the liability not worth it? 

The properties that are consistently booked have game rooms, entertainment decks, views, and hot tubs.

In most states, auction bidders don’t have any opportunity to view the inside of the property before they bid, let alone hire a professional inspector to inspect the property.

If it costs you $100k on a new property as a down payment to save $400/months is that worth it?

The house was 50k total it was funded by my savings, and my grandparents and parents money that was for collage the house is well worth around 145k, I will be using the equity in the house soon to do a short term rental for some high cash flow.