I ran down to autozone and got the stp equivalent filter, put it on, cranked it with fuse pulled, started up nice and smooth and took it for a drive and everything seemed fine, no lights, no weird noises. Not really convinced. Will try starting it without extra cranking in the morning and then following up with hooking up a pressure gauge. I also got a spare cartridge filter to put in to test with the pressure gauge and see if anything changes.

Any updates on this? I have the exact same issue with my 986 and the LN adapter. I changed the oil/filter a week before winterizing it and I noticed the low oil pressure light after a few cold starts. I decided to worry about it in the spring. I am not sure which filter I used - It was either the napa one it came with or a Wix (not sure if I have the XP ones). I did not have this issue last year. Shout out to JFP in PA, I always appreciate your help.

First check which filter number is on the car when the problem occurs to make sure you have the correct filter.

What I think happened was the filter was filtering out the engine restore additive I put in during the last oil change, and it was restricting oil flow since there is no oil bypass with a spin on filter. I found it in the filter when I removed it. Did you put any additives in the oil? I changed the filter twice and have not had a problem since.