What if you plan on Fox Cities or Lakefront and have Whistlestop as a backup if things don't go as planned? You can always register for Whistlestop the night before the race.
Whistlestop is the only one of the 3 that I've run, so I can only speak to that. I can guarantee that it will not be hot in Ashland on Oct 14th. The course (or coarse :- ) is fairly well blocked by the trees, so wind shouldn't be that big of an issue. It's pancake flat, which can be good or bad – sometimes it's good to work different muscles. I ended up running solo from mile 15 on, but that was okay with me because I was feeling awesome. Plus I started to catch people and pass half marathoners.
If you “need” lots of people to run with and lots of crowd support. This is not your race. If you want a low-key race without all the hype where you don't feel a ton of pressure, this may be your race.
Maybe the surface does slow the runners down some, but what it takes away, it gives back with not having your legs feel like hamburger during the last 10k. Plus your post-race recovery will be a lot faster.