1. The starter sounds like it may be an original that never got retrofitted to have the anti-kickback Bendix or perhaps the Bendix was changed but needs work and is now being kicked out of mesh by false starts of the engine. You can check out the operation of the anti-kickback Bendix in the article in this Service Counselor and see if it is something you want to dig into farther.
https://www.packardinfo.com/xoops/html/downloads/SC/SC-VOL26NO9.pdf 2. As Don said, just connect the power leads for the timing light to a spare 12v battery sitting next to the car and connect the pickup leads as per normal.
3. If the engine is starting and the oil pump is providing adequate pressure IMO, there is no need to remove it for anything.
4. The service manual says to adjust the valves as soon as the engine is up to running temp. Didn't see a recommendation for a specific time for a follow up recheck but others may have advice gained from experience.
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