@Andrew MontgomeryNot sure if you can access some of your 401k and roll it into a self directed IRA to start  investing as a passive investor in someone else's deal, to learn while you earn.You are looking at it linearly.

Let the old lease roll over month to month.

Buy a few leads—start with a small test amount—and assess their quality for yourself.

This past summer was our first year, so to test the market we had a 3 day minimum, and we filled every weekend with 3-5 day stays easily but we had holes in the midweek.  

If the goal is still the goal and you are willing to do anything to achieve it, then test everything, don't set a path in stone that you cannot come from out of. 

The thing that got this whole idea rolling is that California just passed sweeping statewide regulations.

This weekend it rolled off just south of $510.

Once you have a shortlist, sign up for an account with each one and test them extensively to see how they function.

I would get the ball rolling with your new PM, onboarding, photos, etc so that once Jan 18th hits they can flip the switch and turn your property live.  

Review all leases and match them with the rent roll and ledger.