So... back to the OP's questions

The amp's looks, tone and vibe - he likes them, but not enough headroom.
After a sevice/recap for a true evaluation of what the amp is like, what next?
Post #8 about (slightly) modding the 50 for 6550s would increase headroom. I imagine this is easily reversible.
Post #14 about *not* modding an unmolested amp to retain its value is equally compelling, especially if you could sell it to help buy a louder amp.
Post #68 slight mod of reducing the value of the cathode bypass capacitor in the first preamp stage to roll off some very low bass for more headroom.
The posts about high efficiency SPL speakers/cabs - all sensible.
So much comes down to how much money does he want to spend?
Is this amp is 'the one' for him? Good tone, good price, mint condition etc?
Would a Bassman 100/135 be a better starting point? - same tone and looks (but slightly taller/wider)
If he replaces the 12" drivers, would a Bassman 100 fit on the 2x12 if he changed amp later on?
Fender has 'matching' 2x15 cabs, but they're bigger to schlep around.
*If* the look and tone of a silverface Bassman *is* 100% what he wants (but louder) what is the 'most sensible'* course of action.
* 'most sensible' need not be 100% rational e.g. some of us really like classic cars even though a modern car would be more sensible for lots of reasons.