While I don’t regret anything in my life if I was to go back in time I would finish the real estate degree and go into something real estate when I graduated at 22 instead of doing it half-as**ed for years.

If, however, there are any gaps at all in any of the above items, even a gap so small a mouse can squeeze through, that tenant will exploit it and your life just became a 7th Level of Dante's Inferno.....:)

I would talk first to an electrician as many do fire alarm and life safety.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I tried changing useful life to 1 year but it doesn't change the line to show as an in year expense.

The tenant laws in New York make life as a property owner way harder. 

And since I would like to go back to it being a STR when some of my life calms down in a year or 2, it doesn't make tons of sense to get rid of it all and then start again!

If the area can support new construction, determine the best style, size, and type of new build for that area.3.

Location. 25 minutes to beach, 40 minutes to Florence, 15 minutes to Pisa, 60 miles to snow skiing.  10 minutes to Home Depot style store, etc.  

Commercial is a totally different ball game than residential, so connecting with a commercial broker will definitely make your life easier.