My wife's grandparents hired Frank Lloyd Wright to design their home, which was built in the early 1950s. 

First, I'd recommend getting to know what different avenues you have such as wholesaling, buy and hold, developing, "house-hack", etc and seeing what you're comfortable with.

I'm guessing I can't be the only one...How do people find comfort in knowing the interest payments, over time, could even exceed the original value of the loan?

Due to the changes with your business, I am not comfortable continuing the current lease.

GCE is designed to protect poorly performing tenants thus, as a side effect will de-house good tenants.

Looking to get more connected with the local investor community on my journey to develop, design, build and hold multifamily properties.

Here are a few simple ways to improve guest experience beyond design and an amazing product (which I highly suggest you have!)

The OTAs are your bread and butter it's good to learn them and then learn all of the intricacies of managing an STR and once you are comfortable that you got this, then look into PMS if you feel like it will help you.  

Curb appeal is a thing, but MTR is about the comfort of home away from home.

But have recently thought about the longer term picture and my passions don’t align with my career even though the job is comfortable and technically what many would call a great spot to be as a Physical Therapist.