Interesting thread. I'm a Louisville native and noticed some well-known investors in town scraping up properties in Portland and wondered why, despite the rock bottom prices. I still wonder why. I think it might be because the city is somewhat tapped out due to the high property demand of the last few years that there really isn't much left but to go into areas that are presumably gentrifying, but actually aren't, or if they are, not at the pace that other cities would.
Louisville is growing a bit, but still has a pretty strong reputation as the opposite of a transient town. Most people here are natives and have been here most, if not their entire lives - or if you're like me, a boomerang who spent 17 years here, then 20 years away before moving back.
Not to dissuade any out-of-state investors completely, but I'll attempt to provide a clearer picture of the opportunity:
As a East End resident for the time I've been in Louisville, the city has had a reputation that anything west of 9th street downtown was to be avoided. This would include Portland. Natives also have an unwavering opinion about New Albany and Jeffersonville, Indiana as well due to older, once valid reasons that have long been dispelled about southern Indiana.
Curious what some on this thread would rate the Portland area as? I can't see it as anything above a C- (on the A-D scale), but would love to hear opinions. With as strong as the Louisville market has been over the last 3 years, and the gentrification of all of the cityburb areas East of downtown (Smoketown, Germantown, Butchertown, etc), you'd think that Portland would have been gentrifying already given its proximity to downtown and a reputation that wasn't as bad as neighboring Russell and Parkland neighborhoods. The Falkner Gallery is helping Portland, but the incident there last year really set the neighborhood back, in my opinion, reinforcing those old native opinions that Portland really wasn't that much better than their West End neighbors.
Add in the responses above of how tough the S8 inspectors are now here and it really makes it tough to consider investing anywhere in the West End, even if the numbers presumably "work".