Your going to have some serious boil off so do a few test runs to figure out how much extra water you'll need to start with. As for fermenting temp, I think I would put a coil in it from the get go. You don't want to rely on the most unreliable thing (weather) to maintain good fermenting temps. Especially when you start making big batches. I would think putting this much effort into it before you've even brewed a batch, that it would piss you off to have just "ok" beer rather than awesome beer due to bad fermenting temps and not being able to cool the wort in the given amount of time to avoid dms!