Nice wood floors but ugly kitchen and baths.  

I furnished 2 STRs for that amount, just go to either high-end thrift stores or a lower-end antique store....you'd be surprised at how little you can pay for solid wood furniture...

We don't have any issue getting it booked up for the season.

Instead you will cash flow right out of the gate and appreciation is faster in those states with TLC properties or adding things like an ADU, or Carriage home on a bigger lot.Most of my investors that live in CA purchase in those states listed above and in most cases its easy to introduce them to local Seasoned realtors Contractors, Handy Men/Women that can help them save money and feel secure about the distance from home to REI.

Often established sellers go with seasoned listing brokers.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

Being fairly new to land lording I felt the need to gather a bit more insight from other seasoned professional with how to proceed, but you're absolutely right. 

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?

I want to ask ya'll seasoned investors if you were starting out today where would you start investing with all the experience and knowledge you have now?

I spent a decade in advertising, before founding and running a custom wood shop for another decade, so 'm pretty good at the self-promotion.I agree with you that the more gorilla approach would be most effective and that's actually what i've been doing – calling RE agents in my service area with active listings, introducing myself to property managers and leasing agents...To answer your question, I will have to handle the work myself for 6-12 months to build out the SOPs and field service management systems, but I have a lot of relationships for those looking to "do the work".I'll check out the meet up and would love to grab a cup of coffee, I'll shoot you an email.