A few quick notes before I go into more detail on how I approach situations like this:- As mentioned in other replies, a 401(k) match should (almost) always be taken advantage of.

I'm a local Denver agent primarily, but I'm familiar with some of the challenges up in the mountains because no deals make sense running the quick math. 

Expenses do not take a break so until you have no expenses taking breaks should be quick and infrequent. 

Listing your property there ensures visibility.Build Relationships: When agents reach out, respond quickly, highlight your property’s amenities, and showcase your flexibility to meet displaced families’ needs.Highlight Insurance-Friendly Features: Emphasize features like flexible lease terms, utilities included, and a fully furnished setup to attract insurance placements.This approach has helped me successfully market to insurance companies.

It felt like everyone I found were self-serving, looking to line their own pockets, or not willing guide because of fear of competition.

Having said that my allocation is flipping quickly. 

That then registers the property at a new “base rate” and your future rent increases all be “base rate” + Inflation as guided by the town.

The neighborhoods are not upscale but they are desirable so good tenants are typically found quickly. 

I know it's a balance of reality, values, and what makes one happy that guide our decisions.

Using a HELOC for the down payment on the second home might be an option, but lenders may require you to wait a few months post-closing on the multi-family before approving new loans.The BRRRR-style approach could work if you can renovate and refinance quickly, but make sure the timeline aligns with your lender’s requirements.