Yes, we discussed this in the past at length and Verslagen and I actually figured out how to install an oil line fitting in the head itself. I have an oil fitting installed on my backup engine that feeds directly to the very last cam bearing on the internal oil passages.
To make this oil cooling idea even start to work you need to use a custom gasket that totally blocks off the oil passage between the right hand oil filter/clutch cover housing and the main crank housing. This forces all oil flow and pressure to go out the oil testing port.
This could provide full 100% low rpm oil pressure to your cam gallery through your exterior piping.
Issue now becomes how do you feed all the interior transmission, crank and such like passages if you do this 100% out the test port trick?
Provide proper oil pressure to them through exterior tubing and you are back into parallel pathways again pressure-wise. But you can use all the oil volume/pressure available running it through your cooler if you do the plumbing right.
But there will be no large volume of flow through the oil cooler doing the trick this way, just what will exit through the cam clearances, crank shaft clearances and transmission flow clearances.
You simply cannot move a large oil volume to "cool the oil" without lowering both oil flow and pressure to the critical internal areas AND the head area. Your oil pump is currently sized to JUST BARELY feed the internal needs with no deflection of the oil flow for any bulk cooling.
=========================
Now, let's play with the ideas a little bit. You say supercharging, but do you really mean turbo charging?
Some of your sketches seem to show a turbo, I think.
Does your turbo require an oil feed and a return feed line?
If it is a turbo, then you likely need to run a synthetic oil like T-6 anyway so the oil won't cook itself solid when you cut the engine off and the hot turbo sits with some static oil in it.
If you are running T-6, then you don't need to do any special oil cooling anyway since the Savage at whatever temperature simply doesn't get nearly as hot as a turbo does.
All big 16 wheeler engines have oil passage turbos on them and T-6 was built for that duty from the get go --- it doesn't care about turbo heat unless it goes way up past 550-600
F.
=========================
I investigated nitrous quite intensely at one point in time as it was the cheapest way to find an extra 25 hp.
I determined that the Savage clutch couldn't take that extra 25 horse power without extra plates and stronger springs.
The SV 650 uses the EXACT same steels and fiber plates that we do, just with two more fibers and steels in a slightly longer basket (same exact construction type, just longer for more plates).
I also determined that the tranny would likely go next after the clutch was strengthened (considering the output shaft pulley splines as part of the tranny makes this just about a no brainer).
I then noticed I was really trying (expensively and laboriously) to bump the Savage up to almost the performance level of a bone stock SV650, so I bought an SV650 and rode it for the most part of a year until I realized that a re-cammed OS high compression pistoned Savage was really enough bike for everything I ever needed.
So, Dave and Lancer have actually built the bike I then envisioned and they can wax my butt at will on a straight away. To outdo them I would have to go nitrous now -- which means the clutch can't take it ...... etc. etc. etc.
Next nugget is that riding with two of these known to be better bikes that I know can wax my butt at will, I still can run at the head of the pack as a pure willingness to put your butt on out there in the curvies is more important than hp.
And the last little nugget for your happy meal is this one, Big Zuk can wax MY butt and all our butts at will on the mountain curvies (run slam away from everybody else) on a bone stock Savage .....
..... unless it is raining on us hard -- in which case Dave will ride MUCH more aggressively because it is really cold and nasty and he really really really really wants to get back to the cabin and get a nice hot shower ....
And the driving rain keeps him from even reading his speedo so he doesn't even notice he's flying along at 75+ mph in the driving rain.