Ok, 50-100 trees is a goodly number. After 6 years I'm up to 50 trees even though I could tap more. On buckets my average yield seems to be about a quart of syrup per tree per season.
So let's do some math... When the trees run, you can get two gallons of sap per tree per day. 1/2 to 1 gallon is more normal but you want to be able to handle a good run without killing yourself. So if you tap 100 trees, you could have to deal with 200 gallons of sap. Good news is you'd make 5 gallons of syrup that day. Bad news is that you have to boil away 195 gallons of
water.
I see boil rates of around 1.5 gallons per hour per square foot of evaporator area that is in contact with the fire. So if your oil drum is 4' by 5' that gives 20 square feet. It's really a curve so there's more area than that but you probably won't have it full so let's just assume 20 square feet for the kicks of it. With a good hot fire, you'd get 30 gallons per hour of boiling. So in a perfect world, you could boil away all that water in 6.5 hours.
Now in the real world, you have to deal with the depth of the sap in the tank. If it's deeper than a few inches, it reduces your boil rate. Ideal is in the 1-2" depth (depending on your pan style). So if you have a foot of sap in your curved bottom pan, that would likely reduce your rate.
Another element of the real world is that it takes quite a while to get a huge tank of 40 degree F sap up to boiling temps. I'd guess at least an hour. Then finishing the syrup adds more time. I don't think you'd be able to boil it all the way to syrup on that curved pan. When you get down to 5 gallons of syrup (or 2-3 gallons on a normal run) the level would maybe be an inch or two in the center but where the syrup gets shallower at the sides it would probably be burning. So you would likely want to take the syrup out early and do the last bit of boiling on a more controllable device (turkey fryer, gas range). Draining the tank and doing that last bit of boiling will take at least another hour or two. Then you have some filtering and bottling time. So I'm guessing you'd be very tired at the end of the day.
I guess what I'm saying is that you may want to start smaller your first year and work the kinks out.
Now back to your questions.. My early arches had cinder blocks on their sides as simple two barrel chimneys. My better arch had two 6" chimneys but I found I only needed one of them. The rule of thumb I'm most familiar with is that the cross sectional area under the pans once you're beyond the firebox
should equal your chimney cross section. So for the block arch in your first photo, once you get a couple feet into the interior of the arch the floor should come up (sand/rubble) and end up an inch or so below the bottom of the pans. That will match the chimney cross section and force the hot exhaust gasses and smoke up against the pans to give a better boil.
If you built the block arch and had it 3' wide and set your 4' wide oil pan on it that would help a lot with the burning of the syrup on the sides. If you use rocks you'd want to explore which ones can handle heat without exploding. Maybe another rural myth but I've heard some types of stone will blow up if they're wet and get hot.
I'd be very leery of using a used oil drum. As you boil down the sap, you're concentrating it. And you're possibly concentrating anything else that's in the pan. The steam pans are fairly affordable on-line ~$25 each. Or cheaper from restaurant supply places or the dump.
Hopefully this made sense, sorry for the length of the post...