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For the most part, the boards I usually ride on Indy in that range, the 8.5 x 32.3 with 14.5 wb and the 8.38 x 32.25 with 14.5 wb often just feel a little long, but trying Ventures on some other 8.5 boards like the DLX shorter wheelbase decks or anything else with similar overall dimensions with 14.38 or even 14.25 wb just seem to work a bit more comfortably for me when the board was a similar length to what I usually ride and much the same middle between kicks with shorter wheelbase, if that makes sense.
Not saying that will fix everything, as it is more the concave and shape of the board that will make things feel this or that way, but having something that is a little shorter in the wheelbase but much the same overall in length means I can ride a board with Venture trucks and not really have a difficult time getting used to it.
When I put Ventures straight on the board I had Indy on before, everything felt super heavy on the manual / pop point, but within a few sessions it got a bit more normal, then when putting Indy trucks back on they felt way too light and it took a bit to get used to that again, all on the same deck.
Shorter boards with shorter middle between concave were way harder to adjust to for me, always having ghost pop and just not working, even though I tried to give it time, but I am sure others will set up almost any combination of truck and deck and not have any issues.