Great post! I've worked quite a bit around the Asheville market for STR investors and I can say that, from an investor perspective, the entire area is full of opportunity across a wide array of investment strategies. To add a little color to the STR strategy.. I'm glad Jarad mentioned the STR restrictions (I wrote a blog around this shortly after the STR laws were clarified by the North Carolina Superior Court in the Wilmington case earlier this year) as they are changing quite quickly in certain mountain towns.
To be clear, if you're in Asheville city limits, most likely you cannot STR a house unless you're in a hotel-friendly zone, and then you need to meet hotel code requirements (open space, common areas, etc..), but the Asheville city limits are not massive, and even some Asheville addresses are not in Asheville city jurisdiction. Here is a very useful link if you're unsure if it's in Asheville city limits or not.
Many of the surrounding towns have benefited greatly from this restriction and have totally revitalized their downtown areas due to the influx of tourism over the last 10 years. A few towns that have been historically very friendly to STRs: Black Mountain, Fletcher, Fairview, Mills River, Hendersonville*, Swannanoa, Clyde, Waynesville, Candler, Canton**, Mars Hill, Weaverville, Maggie Valley, Brevard, to name a few.
*Hendersonville did try to pass an STR restriction but failed. There is interest in the community to limit or ban, so proceed with caution. However, due to the proximity to the Blue Ridge Parkway, I-26, the Biltmore and the Breweries, many have found success and pushed back on this. So far, they've remained friendly and seem to be leaving it alone, but proceed with caution here.
**Canton has a notorious paper mill downtown that produces an odor almost 24-7 that usually travels north-east across town unless a weather pattern turns it to the south, but in general, people vacationing here for the lower prices are displeased. In general, I advise people to be cautious with investing here because this is the #1 negative comment from people visiting here.
Towns around Asheville that I'm aware have new STR restrictions in city limits are: Sylva, Webster, Highlands, and Woodfin. This list is growing as this has become a very popular topic among town hall meetings. There are attorneys state-wide that are pushing back on this, but in general, make sure you work with a realtor/consultant familiar with regulations on STR and know how to qualify at the county, municipal, HOA, and deed restriction level.