Revisiting this a few years later:
-Yes, power is a huge killer. The local public radio station's translator relay runs off the battery/inverter bank for the community building, is on a high rock outcropping/cliff/knoll, and thus electricity is available, at low cost at that as usually the community building gets power from the school generator as the city owns both buildings and that's part of the lease deal for the school district. Even that has its weak point, though, as if someone leaves the lights on at night by accident in the community building it kills the batteries, etc.
-I'm pretty sure the power issue, along with a spot for a tower, is why we still don't have cell phone coverage there either. A few possible places exist I'd put a cell tower, any other transmitter would be logical there too. Was hoping high HAAT for obvious reasons, which would apply to both, but again once you start going up in elevation around there, power becomes harder to come by.
-LPFM would totally be an option, and, as others have said, if non-directional with any kind of elevation or line of sight whatsoever, could get out pretty well. Another public radio relay translator, at 140w ERP, gets out sporadically all over central Southeast Alaska, but sporadic- hoping higher ERP would equal much better penetration. 140w isn't enough to trip that seek all over central SE, though. For those who may look at a map, I lived in/thought about COL'ing Port Alexander- K216AA is COL'ed to Pt. Baker. Up the northern part of Sumner Strait it does well, all the way north up to places as far as Thomas Bay/Muddy River and west as far as Port Alexander, Port Armstrong, Little Port Walter, and Baranof Warm springs are reached sporadically-Kuiu Island seems to be the major killer.
In my total in my head, beer-math engineering, I'd think 100kw at any decent height would cover a lot, especially as strategic a point as a place like Port Alexander is. Definitely all of lower Chatam Strait, likely pretty Far East in terms of Craig, Klawock/western Prince of Wales Island, Point Baker, Port Protection, Petersburg/Kuperanof/Muddy River/Thomas Bay, north to Tyee, Angoon, even maybe a spotty signal into Juneau. (Wouldn't that be amazing? Hit some population base). Being so close to the outside coast, it might even reach down as far as Ketchikan, etc. Sitka might be harder given the mountainous terrain of northern Baranof Island.
The idea, on paper, would be that it'd actually cover something like (my estimate) 80,000 people. What might that do to advertising revenue? It's spread out as can be, but when I lived in Fairbanks the commercial stations had ads for places in Delta Junction and Nenana. Delta Junction is probably almost a two hour drive away- the stations had a wide area of coverage with the terrain there and they and their advertisers knew it. One station in particular had an ID sweeper with a line of "From Delta to Cantwell...".
-Obviously, power, diesel fuel, site maintenance and possible Forest Service land leases would be the biggest killers there are. One possible spot might be the community water tank, already at quite some elevation (probably 500-600 feet?). An LPFM might be a good start?