The community has 120 houses, similar size, all eligible to be strs.

These are NEVER restricted by eligibility of an STR license, some HOA's might have different rules. 

Some of the costs that you are describing may potentially be eligible as start-up costs or added to the basis of the property.

Lenders that are investor focused have recently expanded their guidelines to allow more flexible underwriting and financing terms for eligibility. 

Cities and counties are constantly updating their policies, waitlists or processes and eligibility will likely be the key ingredient to desired usage.

Fundamentally, you want access to industry & schools.

And I also just fundamentally believe that real estate is a good investment right now.Would love to get more of your insights regarding what you think is my best course of action if I decide to buy properties out of state (I.e how to find the right management company, how to do inspections, finding tenants, and maintaining the property).

Many of these buyers have been around 8 yrs or less, and seem to forget two key fundamentals that impact investment real estate:1. 6% interest rates are not historically high.  

Each type of loan has its own features, benefits, and eligibility requirements, so it's essential to carefully evaluate your financing needs and options before choosing the most suitable loan for your commercial real estate project.https://www.amerimort.com/

Fortunately (for now) usually between 5-10% of active homes listed for sale on the Oregon Coast that are either active vacation rentals or are eligible for a new license.