Repairs are a nuisance,  but an expected part of all housing.

In addition because you have 3 units you do not qualify for the owner occupant exemption (that is only for 2 units).  

We are headed out to Bremerton this weekend to see the house we are purchasing in person.

So i am a 23 year old who has worked his butt off since 2020, i currently have 20k saved for a down payment and by the end of the year i hope to have a maxed out emergency fund maxed out and potentially 30k for my house fund.

I have been doing TurboTax for last 20 years and some of my real estate i purchased were in 2009(condo) and 2013(townhome) timeframeSince you purchased your properties in 2009, you likely purchased the properties at a lower price point than what the houses would sell for now.This means that your depreciation would be lower than others who purchase homes now.You should still have a benefit by depreciating the homes.

As a follow up, is 12 months the minimum owner-occupancy period prior to a refi and change of primary residence?

A lot of the STR management companies have contracts with companies to house their employees when they travel for extended periods of time.

All my houses currently have good tenants that pay on time.

I also house hack and rent a room as a MTR and I've gone with high quality items to ensure durability.

Lessons learned: 1) Do a more thorough tour of house before purchasing 2) Have more money saved Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?