In off season when its a mid term rental I manage.

It’s a newly renovated 3-bedroom, 2-bathroom home, just one block from the ski slopes and four blocks from downtown.The current owner has been renting it out for $30,000 per month during the peak winter and summer seasons.

Then there’s this glorious tax season where you realize how many things you get to deduct that others can’t, while sheltering your income with depreciation, and earning tax free income with appreciation.

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?

The key thing to remember about STR in Cashiers is that our "season" is really only about 12-16 weeks.

But if your goal is to cashflow positive from the Day 1, you may find it very challenging due to current day interest rates, high cost of construction and the fact you won't have the efficiencies of a seasoned developer building at scale.

I adjust pricing based on demand, like raising rates during peak season or local events, and lowering them in slower months to stay competitive.

Conventional loans will require 12 months seasoning for cash out and are usually capped at 75% LTV 2.

I have a non-residential commercial mastermind and the fee started at $2500 in season 1. 

I am assuming you know about this, but you may want to consider doing something like a Wally Wrap so that you have an asset to show your next lender prior to your note seasoning.