I am looking into purchasing a second (vacation) home and would love to hear your thought on the pros and cons of going a conventional 30-year second mortgage vs. using a HELOC or Home Equity Loan on my Primary Residence to purchase the second home outright. 

A quick google search of your state indicates the following regaridng timeline to give notice:30 daysFor tenants who have lived in the property for less than one year, or have a lease for less than one year60 daysFor tenants who have lived in the property for more than one year but less than two years, or have a lease for more than one year but less than two years90 daysFor tenants who have lived in the property for more than two years, or have a lease for at least two yearsI'd definitely touch base with an eviction attorney in your state to ensure you are not missing any steps and to have the attorney as a backup option in case the tenant does not vacate easily.

In the six years I've owned, operated and sold vacation rentals on the Oregon Coast the investment landscape has evolved considerably. 

Most nearby cities are the same.Even in the Denver-adjacent cities that do allow non-owner occupied STRs, they vary widely -- some have caps on STRs, some cap the nights rentable as an STR, some cap the number of vacation rentals one owner can have, etc. etc.This is all to say, first know where you can do Airbnb, then start running numbers.

We were there looking for another property that we could buy together on the beach that we could rent out as a short-term vacation rental.We we're living it up and having a fantastic time zip lining, eating delicious food, and seeing the monkeys in the wild.it seems like from the moment I returned from that trip in August 2022 the real estate market completely changed.

Quote from @Brandon Vukelich:If you buy a vacation rental in Hawaii, then you're tied to that location.

You are required to vacate the home before 5:00 PM on December 31, 2024.

I.E. you know the area better than others.Is there a short-term rental market where you vacation at, where you went to college or where you grew up in?

When considering a vacation rental property, it’s essential to have a backup plan and understand the numbers for annual leasing.

Jackson County TDR is working hard to position our area as a year-round destination, and it is catching on, but I wouldn't count on significant, year-round cash flow from a vacation rental here.