See if the coach fits in and then be sure to choose wisely if you proceed.

I’m on the back half of this process now and am confused as to how I “prove” this tax wise?

There are two other places in my complex that are also vacation rentals and I'm right in the middle price-wise for a similar product. 

So find a QI with demonstrated experience and lots of references who is more in line price wise with where you want to be.  

Perhaps @James Wise may be a good resource to you.In Arizona we are able to do seller financing.

A "couple of months" is a drop in the bucket of what you will need knowledge wise before you start. 

For real estate dealings, I’m up at 3:30am, cold brew coffee already made, do everything I need to do REI wise then pack it up around 6am(ish) to work out.

A wise land lord I know says, "Timid land lords raise skinny kids." 

Definitely a personal decision on how much you want to change and/or sacrifice lifestyle wise.  

Usually it means I don;t have to work with other brokers, which TBH, are my biggest headache sometimes.As BUYER:  I think the odds of you being the only guy making the offer and no immediate competition, works better for you price-wise.