I just started milling a couple months ago with my Dolmar 166 and a 36" Alaskan MK III milling attachment from Granberg. I have milled hardwood up to around 32" diameter. Some advice: Keep the 32" bar, and buy a mill that's somewhat oversized for the trees you think you'll be dealing with; this will allow for irregularities in the diameter. If you're going to do 24" trees, then use a 30" mill, which I believe will fit onto your 32" bar if you take the felling dogs off the saw.
Second, for trees of the two-foot size you anticipate, you probably will not need an auxiliary oil tank. I'm sure such tanks are worthwhile but I don't have one, and just turning the oil screw up high, making sure there is a spray of oil onto the inside of the bar-nose cover of the mill, seems to do the trick. My saw has a manual pump built into the handle, so I give it a shot with that every ten seconds or so.
Third, common wisdom on this site (thanks, everbody for sharing - this has helped me to get up and running with confidence; particular thanks to Ken Dunn) is great. Relevant to your planned milling operations, you need to be aware that this is very hard work for the saw, even a big saw like the 066. Give it some help by running a rich 2-stroke mix; many of the guys who run big saws, myself included, use full-synthetic oil (examples are Maxima K2, Motul 800 and Mobil Racing 2T) at 30:1 or 32:1 ratio.
Fourth, I use rip chain that I made myself from regular chisel chain, following the formula on the Granberg (and Madsens?) web site. I have also heard that it is just as well, and less trouble to grind, a regular chisel chain (by regular I mean not skip-tooth or semi-skip) at zero or five degrees, rather than the conventional 35 degrees that is used for bucking.
Probably other stuff I could tell you, but this will do for now, and with you I'll be looking for other posts on this.
Cheers,
Bill