I would also look at your skill sets and go from there.

A few things to consider when shopping for an STR on the Oregon Coast:- Geographic Restrictions: These are small, remote towns.

This approach will allow you to focus on the financial benefits rather than the day-to-day operational tasks.Additionally, consider how this rental income will contribute to your overall financial picture.

I’ve built strong relationships with agents, contractors, and other investors in the area, and one of my contacts informed me that the owner was considering selling but hadn’t listed the property yet.

Setting financial and lifestyle goals and using lessons from your current setup can help.Good luck!

To avoid that, set a firm, realistic budget from the beginning and make sure you stick to it.

It works great for many people -- not me -- but it might be your best option considering your distance. 

- would you consider the regulation/permit process strict or lenient ?

You said yourself this can positively cash flow now, with the financing you were considering.

Those rules are set by Fannie/Freddie NOT your lender, or any other lender in fact.