I only chose wheelbarrow wheels for their carrying capacity, really. The ones I got (solid tires) are rated for 445lbs each.
I'm not too worried about a skirt. When we get snow it's light and only lasts a day or two and there's not much debris around either (leaves and twigs don't count against wheelbarrow wheels). I hear ya on the raceway though - a concrete ring for the wheels to ride on will help decrease rolling resistance, that's planned.
I'm not trying to make it portable though, no way. Once the center bearing is in, that's where the 'mill is going. I could change the top at some point but once the carriage is bolted to the center bearing it'll be there until the wheels need replacing.
Tipping is something I'll have to look at more as I progress but the center bearing should help act as an anchor. The weight of the loaded carriage could be near 3/4 ton if I wanted, and with a 6' dia. footprint, that should help some too. I dunno yet really.
more later I guess...take it easy