As others said out of state can be more challenging based on location but local or out of state both can be done. 

property location/ condition?

@David LewisRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I didn’t see your location in your profile or your post, but assume at least 17% state/federal taxes leaves you with $10k/yr. 

Plenty of STRs that perform just as good as the pool STRs because they have a great design, location, or other fun amenities that have less liability and headache.

I've narrowed down the best return for my money in this market to a 2 bed/2 bath (with top tier amenities) - about 500 total 2/2 listings.I'm finding myself a bit stuck when analyzing why certain properties are making so much higher than the average listings when they seem to have very similar locations, amenities, style, flow of home, beds/# of people they sleep, reviews, number of reviews, etc.

However, what is far more important for financial freedom is the location/city where you invest.The city where you invest is far more important than the current interest rate.

If one wants Precision, become an engineer.

If entities are disregarded, you can keep up with more than 1 in a single QBO account using the location/business feature to keep track of them separately.

I do it manually (and keep in mind, it also depends on the state and location - VRBO does for some and not for others, Airbnb does for some and not for others) I know many folks happy with Avalara though.