Here are some rules:  https://www.nerdwallet.com/article/investing/roth-ira-withdrawal-rules#:~:text=Contributions%20can%20be%20withdrawn%20from,made%20without%20taxes%20or%20penalties.I agree that you shouldn't let the tax implications be the main driver of your decisions, but you do want to be aware of the potential tax implications because Uncle Sam will want his money.

Now that I dont fly anymore  I dont think I will ever set foot in that area its just way to far to drive. and personally not a big fan of the Oregon coast  unless  its Tillamook bay to fish for Salmon and Steelhead in the rivers that feed the bay .. thats the only time we go to the coast.. my wife was born and raised on Puget Island in the Columbia river ( Cathlamet) so she wants a summer home there on the island you can get river frontage and nice sandy beach and watch the big ships roll by.. 

You will also need to determine how much you want to raise.

There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

Start early, raise that equity well in advance, and make sure all those forms and verifications are filled out correctly.

Are you aware of some actual legal authority that validates the IRS opinion on this issue?

I owned for 37 years, raised the rent many times, and later sold for 6X what I paid. 

I find condos/townhomes to be easier to manage out of state because the HOA handles a lot of the maintenance, just be aware of condo fees and find a place that is reasonable like $300-400/mo or less if you are lucky.

Can you raise rents, reduce expenses, or change its use (e.g., short-term rental, mid-term rental)?

Your age might raise some eyebrows initially, but as long as you're professional then you should be good.