I'm building a 462" at the moment that hits many of the same things you're trying to do. A lot of it will come down to how much gear you're going with, and what transmission. I run a TKO500 with 4.10 gear in my Mercury, which nets out at 2200rpm @ 70mph. A drive it on highways and 60mph secondary roads a lot, so my build is dictated by this. The cam profile has to be able to handle 1800rpm in overdrive without balking. That said, I do drive it hard and with the 4.10s I like to have RPM flexibility...in other words have my cake and eat it too. My car weighs 4070lbs, I'd assume your car would be heavier being a wagon. I don't really consider this that heavy if you look at modern vehicle weights, but if going with a mild gear it will take some thought. Trans combo with the deep first gear and cam means I can get away with quite a bit of cam if desired.
My current engine in this combo is a 390 with a 224/232* cam, and it easily pulls the car at 1800rpm and pulls pretty well to 5800rpm with BBM heads. The key is having good flowing heads so you can make the HP goal without requiring a lot of duration on the cam.
I think the builds you're showing are perfect for the combo, and similar to what I'm building. I'll be going with a 235/239* cam, which should scale well from what I have considering the increase in displacement. The TFS heads are small cross section and will give a lot of lowend, but easily support the displacement and rpm I'm looking for, and will do it with relatively mild cam requirements.
As far as being radical at these levels, I don't think so at all. My 390 has a decent idle, but beyond that it's a baby around town, no issues at all shifting it at 2500rpm and just puttering around town. Knock on wood, no issues with the engine at all minus a few annoying leaks. If you want to run 87oct, again I'd think it's just a matter of paying attention to quench distance, making sure compression is reasonable, and making sure the cam matches the combo. I run a true 9.2:1 compresson with the 224* and it runs fine on 87 even though I'm at .055 on quench which isn't optimal (I do run 93 quite a bit, but if I'm taking a long trip I just run 87). Not sure where you live but I'd pay attention to choke and cold start performance if it's a true daily driver. I don't run a heat crossover and have a manual choke, my 390 has always been pretty cold natured. It starts fine in 30* weather but takes quite a bit of fiddling to keep running, and takes quite awhile to really warm up and run well....that impacts the street ability much more than the rest of the combo IMO