Plan Of Action:  I had to shift money around several accounts in order to free up the cash for the repairs as well as the first mortgage payment due in Jan 2020. 

I've had 3 rental properties in the past, which I'm starting to slowly sell off, and would like to shift gears into this land/short term rental industry.

That strategy will shift depending on the property.

Second, since you are new to real estate, realize that these recommendations (and your needs) will shift with time as you gain more knowledge & comfort.  

I over did it on the cost of renovations and the market started to shift towards a buyers market which made me have to come down on price but it wasnt bad.

Personally, I've shifted towards a more conservative approach that takes into account supply and demand dynamics.

I think the strategy needs to shift from income to capital growth at this point. 

If a township does shift their ordinances, owners still have the options to rent for a "season" which works well for places by ski resorts that sell annual passes or communities with amenities like Lakes and Pools. 

If you are anticipating a transitionary period coming up soon where you may have less money coming in each month, like a career shift, and that is why you are wanting a lower monthly payment then again having a bigger reserve in cash you can tap will likely be easier than just plunking more down to reduce costs.

This may not be the type of money you're trying to solve for, but over the past several years I've been gradually shifting a portion of my household emergency fund from bank accounts into I Bonds from the U.S.