This land is clean & clear, knee-high in Coastal (the hay of choice around here), or it pretty much was, until someone mowed it down.

The choice is yours..long term lease gives you, and the tenant the feeling of security.MTM gives you both more flexibility.Which is more important to you both? 

The world will play along because it has no choice.

I properly allocate a percentage of the overall rent to expenses like CapEx, vacancy etc, but on top of that, how much should you have set aside in order to sufficiently cover any unexpected expenses.

Would having good insurance be sufficient for someone in my position or should I just consider continuing with more passive forms of REI like syndications/funds/crownfunds?

One of these alternative options, real estate investments, is appealing to many people who consider using a Self-Directed IRA to purchase rental properties and/or invest passively in syndications.However, just because something is allowed by the IRS does not always mean it is the best choice for your retirement savings.

On the north side where I work, I am much more concerned about loan limits and the self sufficiency test (only for 3-4 units)  I think in all my years working exclusively with 2-4 units only once was something triggered by the FHA inspection, and it was a flat roof the seller sealed off access to decades ago and hadn't been up there to even check on it in 20 years. 

Another thing to note is if its a 3 or 4 unit, it must pass the FHA self sufficiency test, which at times, makes it harder to get loan approval.

Payments were pretty steady last month, no foreseeable difference.Portable storage is when they deliver the storage pod to your location of choice.

And there are first time homebuyer conventional loans that start at 3.5% down.House hacking is a good choice in this region.