I have asked a lot of questions regarding building a high performance cleveland for the street and occasional open road events. It looks like no matter what you do, the strength of the block is a limiting factor. For my use, I concluded I can get into the low 500 FWHP range, and a 7000 RPM redline. If I exceed either, shortened (maybe really short) engine life will probably result. It also appears that the 377 kits work very well within this envelope, and does not shorten engine life.
As far as the oiling, the first thing is a restrictor kit, both cheap and easy to install if your engine is apart. You can not use the complete kit with a hydraulic cam because you need the full flow to the lifters, so I went with a solid cam.
The second level appears to be to add a shunt from the pump to the oil pressure gauge tap. Basically this provides a direct path for oil to the sometimes starved rear main bearings. The negative aspect of this mod is having an exposed external oil line, but I think you can run this through the valley also.
A lot of people run high volume or pressure pumps. If you do this, you may destroy your distributor gear, with the resulting collateral damage (the oil pulp stops when the gear goes). Because of this risk, I am using a stock pump.
Dry sump systems may be the ultimate solution, but every added moving part, or exterior oil line, is another failure mode. If you aren't maintaining your car like a race car, dry sump is probably not a good solution.
Ken