OP your engine operating temperature will not be affected by the oiling system you choose, side oiler or top oiler. The
oil system only determines how lubricant is delivered to the engine's internals.
Your engine operating temperature is going to be determined by your cam choice, how you phase it to the crank, your ignition timing (initial, total and how fast you bring it in), compression ratio and
how the finished engine is tuned.
Once you have completed your build and before or after you install it in the car you would be doing yourself a big favor by taking the engine or the engine and the car to a dyno shop to get tuned. In the car may be the better approach because you will be using the cars fuel system, cooling system and engine management system, if you choose to go EFI
If you opt for carbs (like most of us have) the proper fuel delivery will likely require more than the simple jet and power valve changes most of us are familiar with. You could end up in the emulsion tube and air bleed adjustment sandbox and your best friend will be the guy tuning your engine on the dyno and the oxygen sensor he places in your exhaust.
If you just put it together and SWAG (Scientific Wild Ass Guess) the tune you might get close but then again you might not — more often than not the answer is the might not side of the street. If you go to a shop that specializes in tuning carbureted engines he should have all the carb fuel delivery components you are likely to be needing.
Many dyno shops today specialize in EFI managed engines. There is a very real chance they will not have adequate familiarity with carbureted engines (or air bleeds, emulsion tubes etc) to deliver on the tuning promise for you. You need to find a shop that specializes in carbureted engines. That will not be easy but it is essential.
In the end you will have a properly tuned engine that has gobs of torque and power and good street manners.
A good shortcut on all this work is to go to Bykins or Kraft and buy the finished engine from them (you can ask them to use your block if that's important to you). They not only have two truckloads of experience but they have run their configurations on their own dynos, tuned them on those dyno and produce well tuned, well mannered, high power engine packages for guys like us.
Parting thought, medium riser heads are not hard to find. Low riser heads will leave you disappointed in the power department. Low riser heads will be less expensive but not a lot. Reach higher, you won't be disappointed. Either of the two engine builders can easily help you out in the head sourcing department.
Throwing caution to the wind and taking a DIY shot at this is probably not a very good idea. In the end you will spend more and get less — when you didn't need to.
Ed