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The Bandit 250 or 280's look pretty workable for a modest operation and still doing a bunch of pruning. Maybe keeping your chipper as back up and for some prune days.

150 is not enough of a jump for good machine feeding. It's not just how wide the infeed rollers go, the dia of rollers and hyd power to rollers mater too. If you're pretty sure what you want, try to go help a tree service for a few hours or a day that feeds the type of chipper you want with...

That Wisconsin engine appears to be the higher horse power model, 60 horse instead of 37? That would probably tend to make it a good performer for a hand feed pruning operation. And, it would suck even more gas. Sounds like you are beyond that Sean - bigger capacity, machine feed.