It takes some time to gain traction as a new rental & it sounds like you will not be able to launch the rental until after prime Summer season, so you will need to be prepared for that as well! 

Licensable vacation rentals are obviously in high demand and offers can become quite competitive, I don't have any formal statistics but I'd say a quality active or eligible vacation rental sells at least twice as fast as a non STR property, the majority within days..My best advice to investors shopping for a hot or high demand asset class is:- Prepare & Practice: Get your ducks (GO UO!) 

The prepared me a quote that is low price (That is nice), but I am not sure if I am covering all the bases.

If you go after the comps the appraiser used, be prepared to explain why your comps are more appropriate.  

And no, I have not spent much time on preparing or marketing, it was simply about paying it forward to newer investors in my city, however it provided some interesting insights. 

I learned how to prepare all my tax returns, and realized it is better done by a professional who can keep up with the changes in tax law.

I'm not saying the next light bulb won't be invented (it took 10,000 tries) but plan on a long slog to make it happen in real estate.We and our Joint Venture partners use a fairly sophisticated spreadsheet with a lot of automatically input variables and at the end of the day, it is still experience and second guessing the market that works best.

You prepare for the next market cycle in the existing cycle.

As I go through this journey I have also decided to educate myself in real estate investment so that I can be best prepared for July 2020, this is the point when I will be debt-free and will be shifting all my energy to actively investing in real estate utilizing the BRRR method.To that end, I have made it a goal to analyze 2 properties per day so I can become familiar with my area and become comfortable analyzing properties...and that is where my issue is.

There's lots to do and learn so be prepared for that.