If Cabo gets a better GPS option in the future that will alleviate a lot of those issues, until then do it ourselves or PM. 

Consider hiring a property manager as it can alleviate the burden of managing the property by yourself.

And here in the South, we build or always think about ways to reduce or alleviate the Heat! 

The tenant in common (TIC) structure alleviates this issue since you are acquiring real property.  

You can also pay yourself in December for the year and alleviate any penalties if you would have any.

Having others to vet the deal with helps alleviate the fear.

These factors should alleviate some of the low season drop off and provide some additional exit strategies should things go sour.

Have any others of you had any fears like this and is there anything I can do during my waiting period to alleviate some of these fears?

I've used a similar service called Rhino at an old brokerage that alleviated the pinch many tenants experience in coming up with security deposits, but those terms were negotiated at scale (we had over 13,000 doors under management).

I tend to get a little wordy and muddle my thoughts sometimes, and typing rarely alleviates that ailment.I understand the basic calculations for and have a spreadsheet put together that shows me how many properties I would need for $X/month of income.