BeerSmith 2.0 will also tell you how much room you'll need to do the mash-in, and mash-out for your recipe. I just make sure I keep it under ~9 gallons for my 10 gallon RubberMaid mash tun. If I need more space than that, I can switch over to my 70qt Coleman Xtreme cooler mash tun...
IMO, you won't regret having a larger mash tun. Unless you're fortunate to have buddies that will let you use their larger mash tuns, when you're going to mash more than ~14# of grain. For me, a 5 gallon cooler/mash tun just didn't make sense... Especially since my low OG batches have 12-13# of grain, my 'normal' batches range 14-18# of grain, with 'big' brews going up to about 28-30# (5-6 gallons into fermenter) of grain.
I have started to do the mash-out with the past few batches. I'm getting good results from this method. The real test will be once I start drinking those brews. So far, they're either still in fermenter, or chilling down before being opened.