Bryan,
If you are getting visible oil into the heads after cranking then it might simply be a sensor problem. If you can't see oil in the heads, then you might not actually be pumping oil thru the engine like you should. This could be due to the oil pump not getting or holding a prime and not actually drawing up oil from the sump to distribute to the galleys. Another potential problem could be the oil pressure relief plunger is stuck open and bypassing all the oil from the pump back into the sump.
An alternative to pre-oiling via cranking the engine is to build a pressure-pot pre-oiler. This is super easy using a small garden sprayer (E.G.
https://www.homedepot.com/p/HDX-2-Gal-P ... /307766539). You'll cut off the spray wand from the flexible tubing and then connect the hose to a barb fitting temporarily installed into the oil pressure sender port (example:
http://sonex604.com/misc/pre_oil.jpg). You then fill the sprayer with a 5-qt jug of 30-weight oil (the normal 20W-50 is a bit too thick to work well in the pot), pump up the pressure (which is what the sprayer is designed to do anyway), and then transfer the oil in a pressurized stream into the engine. Do this for about 20 minutes, draining and recapturing the oil into the pot if needed (or until you're satisfied with the oil reaching the heads). After it's all pre-oiled, drain the old oil, install your run oil, and crank again to check for pressure readings.
It's personal preference, but I like to do the first start with the 10W-30 oil (same oil used for pre-oiling). It starts a bit easier, being thinner distributes better through a tight engine, and you're not going to run the engine hard the first start anyway. After the first start or two and 5-10 minutes of running, drain that oil and dispose of it - it has served to flush any debris that may have been created or knocked loose from the initial run. This gets any of that stuff out of the engine right away and makes the pre-oil serve double-duty as flushing oil.
The AeroVee uses the alternator output for RPM readings. If you aren't getting RPM displayed, check the wiring from alternator to voltage regulator and see if something is amiss.
Jeff