As you might already know, house prices in New York are extremely high, which makes it financially difficult for me to try house hacking here at the moment.

Hello, great question as I am considering them too, not specifically looking into using any form of retirement accounts for initial investment though. 

While this would not necessarily result in immediate taxes (because it can be offset by your lifetime gift and estate tax exclusion), a gift tax return (Form 709) would need to be filed.

Quote from @Sabrina Marie:Went back to looking at Digb and Quickbooks and made the move to Digb so I don't need to setup multiple subscriptions for each LLC, it isn't setup out of the box for real estate and I'm not an accountant/don't want to pay someone to set it up for me.

You may make $50k on a flip but have to wait 6 months from list. ( in specific areas - not all of CLE)As a full time investor turn time is hyper important for me to turn my properties and money over as many times as possible in a year.Another example is are you a flipper or a renter.

I would suggest coming to some investing meet ups and just start talking to others and form a plan based off of that.

New cost for me: $425K  Rent: $4200. 

Quality over quantity for me. 

Over time, I hope to try a variety of strategies to see what works best for me as I grow. 

For me, my clients are seeking high-paying guests who leave raving reviews, which in turn drives better bookings, not just more bookings.