You can hire a vacation rental management company to handle some or all of this.

If they get most or all of their capital back and still retain ownership, we have done a good job and they should be happy.

Is your property zoned for 3 units, is it a legal 3 unit, is it legal non-conforming, is it an sfr + adu's or? All

Or all. 

If you have the time or are particularly handy, you might do some or all of this work yourself.

.), or buying, selling, leasing, or certain neighborhood classes, or something else, or all of the above?

It’s a business, it needs a in-person contact to operate optimally.A full time employee probably doesn’t work every day of the week, or all open hours, every day.  

Some or all of them will stop paying rent, so you may get 1/3 or maybe 2/3 of rent for a month or two.

With no W-2 income I'd want a minimum of $10,000 per unit set in reserves.Also, I'm assuming your current employer is paying for part or all of things like health insurance, retirement plans (Social Security, if nothing else), short and long-term disability insurance, and possibly some other nice perks that will be your own to foot the bill once you go full time RE. 

For the most part you are correct that the new depreciation may offset some or all of the gain from your sale, but it may or may not cover all of it, and depending on your tax classification, it may not work.