It is located on a very scenic setting.

location.

Unless y'all have an incredible W2 to help with the purchase, you will not find something that "works" in the Triangle and in a good/safe location.

I’m open to exploring those locations since they aren’t too far of a drive.I’m leaning towards a SF property because I have $10,000 to put down, want to stay within my budget, and being new to this, I’d like to start small.

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.

Where is your property located?

But, it may not offer the ROI as other locales, and it may not be "fun" like buying in a favorite vacation spot.2 - The highest ROI folks - Self explanatory, will go where ROI is high and/or regulation low.3 - The second home/retirement minded - These people are looking for minimal ROI but want the house in a specific location because they like to use the property and want it to pay for itself.

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. 

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. 

The property is in a great location,  close to stores, restaurants, fair grounds, freeway access, and less than a mile from hospital.