For a more general philosophy on hospitality, especially if you are going into the higher end STR space I would recommend Four Seasons: The Story of a Business Philosophy by Isadore Sharp about the founding and development of the Four Seasons brand. 

You'll be able to meet seasoned investors that can direct you in the right direction.

I am looking for advice from seasoned house flippers, both in my local market and otherwise with a track record of success; or even with sound wisdom that can be applied to this potential deal.

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

It’s a short term rental started in Oct 2024 and earning during this off season is under $10K but cost segregation has nothing to do with rental income only depreciation of the property and with bonus depreciation being 60% this year I think it’s worth it.

I would be interested to see what the seasonality is.Packwood can be tough to get to in the winter.

I would check this out with a seasoned securities attorney for their opinion/guidance.  

From the financing side of things - keep in mind that conventional cash out refinances require 12 months of seasoning in order to use the new appraised value.

Not likely), vacancy (@ 8% for me), and a possible PM (10% normally).I recommend you reach out to a local seasoned investor and have them run your #s with you, as the #s depend on how you manage it (how hands on you are) and also local pricing.

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