This was my first tenant occupied visit and my second ever property visit. 

For example in many jurisdictions I can STR units in a duplex but cannot STR an ADU (some jurisdictions will let you STR if you owner occupy).

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

Generally, SBA loans can only be used directly for real estate purchases if the loan is being used to purchase a facility for a non-real estate investment business that will owner-occupy at least 51% of the property.

However, keep in mind, you will have to notify your insurance company that the property is no longer owner occupied but rather a rental. 

The surrounding neighborhoods (West Passyunk, Girard Estates) currently have pretty strong fundamentals, although weigh towards owner-occupied.

If it's an owner occupied unit sometimes I've found the big players like state farm to be pretty competitive on price. 

It sounds like you will actually occupy the home in Washington for a majority of the year, and then travel to Aspen during ski season.

It has stayed occupied with tenants since i purchased, i love how it is completely hands off as well and i don't have to do any management and still get great returns. 

Typically owner occupied multi families are the best kept.