Hi,
The OP hasn't said which PICaxe he's planning to use, nor if there are any spare pins. But personally, I'd Keep It Simple and Safe with a single PNP transistor. That should drop no more than a few hundred mV (hFE = 20). But we also haven't been told the LDO type, nor if the "5 V" rail is regulated, or just a typical "3 x AAs" PICaxe supply.
Two issues worry me about parallelling PICaxe pins. First, bear in mind that the M2s "remap" their port pins, so the PICaxe "virtual" Port B (and C) actually uses the base PIC Ports A and C (and maybe B as well), so they may not switch at exactly the same time. Not that I'd expect it to damage the chip, but it might cause an unexpected reset.
The second factor depends on how pessimistic you consider the Microchip specifications to be. The base data sheet (for the 14/20M2s) only "guarantees" a pull-up current of 3.5 mA with a 700 mV drop (from a 5 volt Vdd rail). That would need a lot of output pins for 50 mA !
Cheers, Alan.