I doubt your issue is IP or timing related, I'm still thinking a glow issue but voltage related, think about it in very cold weather batteries become less efficient, any resistance in the circuit exacerbates the issue, so poor gnds, corrosion in wiring, 1 of 8 glows weak, dirty contacts on glow relay mean less juice overall to the glow system.
IIRC you said you checked glows, how, with a DVM ??? they can read good but still be bad, bad in that they don't fully glow, only real test is to remove them and put voltage to them they should get hot tip to center cherry red quickly 4-5 sec, if longer than that or no full glow then the glows are weak. I've used a batt charger, (MAKE SURE YOU AREN'T ON START POSITION /HI CURRENT CHARGE) safest way is jumper/alligator clips to the glow/batt, they will get hot so need to be placed some place safe for high heat.
Another possibility is in cold weather one of the two batts are starting to get somewhat sulphated & nearing end of service life, which is why I recommend a load tester be part of every 6.5er's tool kit, you can get a cheap one from harbor freight for about $20, since everthing on these trucks is voltage sensitive, everything that goes odd with them requires knowing gnds and batts themselves are up to par.
Last piece of the puzzle, how much juice during these cold weather hard start events is coming out of the glow relay, remember the glows are 6v heating elements, that we juice up to 12v to make them glow. hit them with <12v and they aren't going to get as hot, so put your DVM on the outlet of the relay and see if you are getting a huge volt drop.
Make sure your park brake is on also, on 98 you have DTRLs, which will come on inbetween cranking and pull the batt down even more. What series of glow do you have if 60gs you can add in a pre glow feature, this is however if you find no issues with your glow system/batts. With a springloaded momentary on pushbutton switch wired to apply +12v to pin B of your glow relay you can preheat the pre-cup chamber before attempting to crank the engine at all.