4000' climbing over 100 miles counts as a flat race, so you won't need to run many hills in training. however, even doing 3hr long runs wouldn't cut it.
I suggest that you go get your sub-2:30 before you try to run a 100 miler. you might ruin the rest of your year and any hope of racing a marathon.
I'm about a 2:30 guy...and here's how my training would change:
training for marathon:
75-100 mpw, mostly around 80-90. maybe one or two doubles per week. one workout and one hard long run per week. run trails a couple times per week just for the love of it, but don't seek out hills necessarily unless you're training for a hilly marathon
training for a flat 100 miler on dirt:
80-110 mpw, mostly at slowish paces.
occasional road workouts when I'm running with friends, such as a progression long run of 20mi, avg about 6:30s
long runs go by time, not distance and would be 3hrs most of the time (20-25mi) but occasionally would do back to back long runs of 3/4hrs or a single 5hr long run.
would end up doing way more hills just because the local trails are hilly. the more hills, the better, even for a flat ultra (as long as you don't need to hike those hills too often due to the steepness)