I agree with John L But check the primary fuel system form the tank thru lift pump and filter to the VP44. Look for air in the system!! Use the troubleshooting guide from Blue Chip's website (it is very helpful) I had a problem very similar and fought it for 6 months and all of the symptoms that you describe are what i fought!! The problem was that air was getting into the primary system from (of all places) a fuel pressure sensor on the filter canister top. I probably replaced the frame mounted pump (Holley Blue) unnecessarily, I still have it. My problem started when I was chasing failing or waneing fuel pressure issues and one at a time I first replaced the frame mounted pump and filters, then next the fuel pressure sending unit and this fixed the failing pressure problem and then shortly after this I started having the starting issue, turck ran fine after I could get started. I fought it most of the winter and a couple of times while in the mountains with snowmobile trailer, I had to use ether, hated to do this, but no options. On a good day above freezing in early April, I replaced the bypass relief on the VP44 to no avail and only by chance before I was going to put in the clear Tygon tupe from the filter to the VP44, I saw air bubbles comming from around the fuel pressure sending unit on the top of the fuel filter, removed it and carefully teflon taped the theads and replaced it tight and problem went away and has never returned. I kept going back to Chips troubleshooting guide (Thanks Chip)!!! Be careful with teflon tape in any fuel system!!!! Loctite makes a thread sealant which I prefer in fuel systems and hydraulic systems, but I did not have any at the tiime, but I learned years ago how to use the tape if necessary. Hope this helps.
gtwitch in wyoming