I have considered going with short term rentals in the more vacation type areas in the mountains, but so far haven't found anything I wanted to pull the trigger on, mostly due to being remote.

My guy is good, but he's also too busy for his own good, and thus leaving money on the table.

More than once I have gone straight from the closing table to the bank to initiate a refi that same day.For now you're probably better off waiting out the 6 months and taking advantage of the better terms you're getting but at some point you will start buying properties using your LLC and embrace the world of commercial loans. 

is 100k enough to bring to the table for a new investor into a deal?

Keep it about the seller and the benefits do you bring to the table.

We never get crazy snow here because the mountains deflect the bigger storms. 

I would say not to be so naive and think they're motivated enough to leave $100,000 on the table.

I simply do not know enough to say that a 5/20 year balloon was my only reasonable option on the table.

Looking at properties in Smoky mountains area. 

Here's a table of the number of years, given a rate of return you need to turn $1M to $5M.