In my experience most states have similar laws, though the specific requirements may be somewhat different. 

I live in New York (for now 🙄) and will be buying investment property outside NY state.

As stated above I attended his seminar about a year ago, and to date I've done two deals.

Probably has incite on build costs. site and state specific.. no way to just ball park it. 

The Augusta Rule, known to the IRS as Section 280A, allows homeowners to rent out their home for up to 14 days per year without needing to report the rental income on their individual tax return.Originally created to protect residents of Augusta, Georgia who would rent out their homes to attendees of the annual Masters golf tournament, the Augusta Rule applies to any taxpayer who owns a home in the United States, provided that your home is not your primary place of business.How Does it Work for the Homeowner?

I can certainly see what you mean about using SALY as a friend for most years, but unless you want to stay current on all the state/federal income tax laws, you may want to seek out a professional every few years to double-check.

However, given our current state I'm preparing to set-up my own website and/or post on various channels that don't appear to offer the host insurance and I know asking the Guest for security deposit or to run background checks can be a deterrent for short stays.

or are you open to investing out-of-state?

Hey Team,  So as the title states, I am late to the game as I just turned 52. 

Rental market in NYC moves pretty quickly and will be hard to coordinate from out of state, unless they're ok with their broker doing virtual face-time tours.