You kinda answered your question already, imo: 144. 'cause you don't mind a little magic carpet. You can play around with washers on them. But you can't make 149s smaller. And I noticed they are more like 153mm, if you run them with one washer on each side of the wheel, btw.
It really depends on the width of your wheels though.
I'm currently running F4 55mm Og-classics on Film Trucks (machined to 149mm) on the 1991jr.
The outside of the wheel is flush on the back with one washer; the trucknut is still a few mm in on the front.
I like it this way, but this is my transition set-up. I have no intend to flip it
I had a P9 shape, which is quite similar in width; a while ago, that I set up with Indy 149 for bigger Transition; and then Ace Classics 44 for more versatile use. I was running that with two washers in and 37mm wide wheels, though.
I think you always have to compromise a bit on those tapered shapes...