The external oil coolers are tricky to purge the air, not sure if that's your problem or not but it sounds like you've attempted to correct it. I still think you should check the cartridge filter, if that were to clog the oil flow would be seriously restricted. I replaced mine and the oil temps went down. But the "aeration" I'm talking about is like "oil foaming". Most of the time, the fluid level is not correct. If you get it right, the CVT is very quiet, get it wrong and it will whine. It'll cause transmission overheat, oil pump pressure issues, reduced performance, etc.
The oil lube circuit is a separate low pressure circuit, so I suppose a slug of air in the oil cooler wouldn't make it's way into the valve-body directly. Anything lube related get's either dumped into the cartridge filter, beehive cooler, bearings, & pushbelt oil injection coolant jet, finally into the sump thru gravity. The lube circuit relief valve inside the valvebody dumping anything back to the sump if the coolant circuit become obstructed. I'll have to review the lube circuit again. It sounds like the oil flow in the cooling circuit isn't there, the cartridge filter I'd check first. These cheap coolers also have some decent pressure drop, combined with small oil hose diameter, might cause a problem.
As far as my setup, I haven't run my setup yet, I'm hoping by end of fall but it won't be in time for the summer temps. It's been about almost 2 years on build/development.
The engine is in the final stages of machining process to rebuild it, re-polished crankshaft, upgraded forged rods, upgraded forged pistons, RS oil pump, RS rod bearings, cometic head gasket, the cylinder head is fully ported w/3 angle valve job, custom upgraded springs/retainers, upgraded Crower regrind cams. The CVT is fully rebuilt and upgraded with: Rebuilt/reman CVC torque converter, custom higher capacity 4-clutch forward clutch packs, improved clutch pack release gap clearances, upgraded high torque pulley sheave axial bearings (i.e. cobalt slider pin vs. 6mm ball bearings), upgraded Sonnax oil pump flow regulator valve w/brand new OEM oil pump, brand new valvebody (OEM), latest TCM reflash, custom reinforced forward clutch drum (pending the machine shop), latest factory updated CVT pushbelt 90183, running the high torque AMSOIL synthetic CVT fluid. That's what's done already sitting on the bench, minus the reinforcement insert for the clutch drum I designed, that'll take another couple months to retrofit. The custom Laminova CVT cooler will also have a full flow oil filter like an engine oil filter for improved filtration capacity, plus the oil pan has an additional pan magnet installed already for improved debri pickup. That custom oil filter mount I rapid prototyped and it's sitting on the transmission sitting on the bench, need to get off my butt and send it to the machine shop but it's lower priority for now. Most guys don't know but the stock CVT filter can restrict the oil cooler.........then the oil temps get out of control. When I swapped mine my oil temps dropped, so something to watch out for on maintenance. My solution will make oil filter changes a snap, plus have much higher capacity for filtration.
The CVT filter housing is custom machined, uses a Setrab oil thermostat & Setrab oil filter mount, plus an automotive style filter w/14 micron rating. The Laminova cooler (not ordered yet) mounts at the base of the radiator, replacing the stock radiator hose plastic joint fitting & mounting point and slips neatly in it's place with minor trimming of the radiator hoses. The Laminova cooler is like a super-beehive cooler, much more efficient. I relocated it so I had room for a bigger oil filter, and cause it looks baller......lol. Anyway, all the radiator water flow passes thru the oil cooler, while the CVT oil is pushed thru in counter-flow using the stock CVT oil pump. The CVT oil then stays at between 85*C and a max of about 98*C or thereabouts. Kinda important to keep the oil warm in that range in terms of oil flow and where it needs to get to actually lubricate and flow correctly thru the many orifices. The setrab fanpack cooler is there actually the engine oil cooling instead, which will take the heat load off the engine and give some back to radiator cooling capacity back to the CVT, or I'll run it in parallel with the stock engine oil cooler.