Tone arms can always be upgraded, and to just about any arm, only depending on how willing you are to do (or pay for) the work, and modify the existing table. Which depending on the arm in question might be surprisingly easy or near impossibly hard. So that's the real question: which arm? Origin Live are highly recommended and greatly simplify things as they all use the standard Rega cutouts.
That being said you're messing with the source, arguably the most important component and one you sure seem to like and one you and it seems everyone else thinks will be hard to equal or better, so I would counsel extreme caution.
If space really is tight I think your integrated amp idea makes a lot more sense. Only drop the inboard phono stage idea, there's just no way you're gonna get good sound and why when something like the Herron is so reasonably priced?
You already have experience with Prima Luna. Seems to me you could sell that, and the Pass amps, buy a Prima Luna integrated and Herron phono stage, get a nice bump in sound quality and maybe even have money left over to put towards a nice Origin Live arm for the VPI.