Installing the HV oil pump will give you a nice improvement in top end cooling. Ordinarily, I'd be shocked to see oil temps top 200F/95C at speeds below 40-45mph, even in 95F ambient air temp. (Yes, ambient air temperature affects peak oil temps.) This assumes full break-in (no abnormal frictional heating) and proper carb jetting. Power requirements don't hit the steep part of the curve until 45-50mph. Going from 50mph to 60mph, requires ~60% more hp...that's where the heat generation increases dramatically. There's nothing remarkable, or mysterious, in the least about this, it's basic physics.
The "wild card" in your build is the painted head. I really cannot recall anyone doing this. Above 40mph, any battery-operated fan that this electrical system could power...would be an airflow obstruction. The good news is that airflow...and with it, air-cooling...both increase with speed and those increases are proportional to hp requirements. IOW, there's a self-balancing effect with air cooling. You know how aerodynamic drag increases with speed? Well, this is one positive effect of it.
I suggest carrying an IR thermometer with you, during your testing/tuning/break-in phase. If you see temps above ~250F on the head, or cylinder jug, anywhere but near the exhaust port, you have an overheating issue. OTOH, temps below that level, plus dipstick temps below 110C should mean you're okay.