The oiling system has more cooling effect on the engine than the cooling system itself.
This is not correct. The coolant has far more effect on the engine temperature than the oil does, which is why the chambers (the primary source of heat in an engine, by a long shot) and cylinders are cooled by liquid (or air) rather than oil. Oil's primary function is lubrication, while its cooling effect is essentially a bonus. Oil is not exposed to the truly-hot surfaces of the engine; a rotating crankshaft or cam simply doesn't get terribly warm due to the
lubricity oil provides. This is why the vast majority of cars don't have an oil cooling system; in most cases the oil will never reach 270° without one. Adding a ginormous-by-huge oil cooler will not solve an overheating issue in most cases.
As far as performance and longevity, you've simply got to choose which one is more important. As 68R/T stated, ideal oil temperature is generally in the 230-260° range. Towards the upper end of that scale (and beyond) is where you find better peformance, while at the bottom is where the longevity lies. You could get your oil temps lower than coolant temp with a huge oil capacity and large cooling loop, but at those temperatures
it creates sludge. So even though the oxidation rate for pure petroleum doubles for every ~20° beyond 150°F, a little heat is a good thing. Besides, the additive package lowers the oil's tendency to oxidize so quickly.
Another aspect of oil temperature is its effect on flow. The hotter the oil, the better it flows and the easier it is to pump through the engine. Hot oil means free horsepower due to lower pumping losses, which is why many professional circuit racers run their oil hot (300° or more) as well as lightweight--the heaviest oil you'll find in a NASCAR pit is 5W-30, and that would be at a superspeedway. In qualifying, they'll run as low as 0W-10 depending on track length. Testing has been done with synthetics, both in the lab and on the track, at temps as high as 350°! Of course, you can't buy the oil they use, and they rebuild the engines after every event. This approach isn't exactly a street-oriented idea, but at the same time, sub-coolant oil temperatures would actually have an observable negative affect on fuel economy.
Many large over-the-road diesels actually use an oil thermostat to route oil through the cooler. Now, those guys need to not only get every mile possible out of their oil, they absolutely need to get every mile out of the engine itself. They're also measuring their fuel economy in tenths of a MPG. Those oil thermostats open the cooling loop around 255°F and close (bypassing the cooler) around 235°F and below.
Unless you've got something in your combination that would generate ridiculous heat in your oil, such as high bearing surface speeds (due to sustained high RPM and/or really-large bearing journals), turbochargers, etc. oil cooling probably isn't necessary. If you want one for piece of mind, that's fine, but don't go crazy with one big enough to block the radiator. If you're looking to monitor it, the standard place to check it is at the point where the outlet to the cooler would be, in this case right at the outlet of the oil pump (the same is true of transmission-temp gauges; they should be in the "hot" line to the cooler as close to the transmission as possible).
Use good oil. Change it regularly, either 3,000 miles or the manufacturer's recommended interval. Oil in a carbureted or even TBI engine should be changed every three to four months regardless of mileage; carbs/TBIs dump fuel into the oil and break it down much more quickly than port-injected vehicles do. Obviously, if you change the oil and park it for the winter shortly thereafter, there's no need to change again it come springtime, but if it's being operated fairly regularly, that oil's breaking down in the pan even while parked. Used oil contains corrosive agents and absorbs moisture much better than fresh oil, so if you store your car for months at a time, change the oil before you park it, rather than when you bust it out from under the cover. Or, do both. Oil's cheap. Engines aren't.