Moreover, even if you decide to go the commercial route, given your age and current position, I still highly recommend the investment strategy of house hacking.

HelloWe travelled to tarpon springs with my wife in March and really loved the area and the parks/beaches there.We are thinking about buying a vacation house/ investment property there.

Also, some concern on the $5.3 million in transaction cost to acquire the property approximately 9% of the deal, obviously there won't be any money set aside for renovations given that the property is only a few months old, so this is all frictional cost to the investor. 

The agent came the next day with the buyers and I spent a couple hours going through the house with them.

Even if you are looking at buying multifamily all housing is connected.

ya well cupertino palo alto los altos and los altos hills Monte vista Saratoga Los gatos still basically $2,000.00 a sq ft for SFR housing..

The government grossly overstimulated the economy, increased the money supply by 40%, and caused record inflation (in housing, food, energy, everything).

So, do you have any advice for a first-time house-hacker wishing to jump into the appreciating deep end and swim with the sharks? 

I see you're from Hoboken, where are you looking to house hack?

The house I am looking to buy has a detached garage about ~1300 square feet and already has a bathroom in the property.