Hope this helps.
I have a flipside 400 AW and my 1DX, with 70-200 F2.8 II happily fits with room to spare . That combo is ~38 cm long.
When I fit a 2X, it becomes ~ 42 cm long and it JUST fits in the 400AW.
I have had the same question, 300 vs 400 and I am happy that I decided for the 400. It takes the above plus a 16-35, 24-70 and a 100 mm macro without any problems.
I find that the 400 series are a similar size as a normal daypack for hiking.
The internals of the pro-trekker are very similar to the flipside that I have, the only difference is that the flipside opens at the back. I find this usefull, because when you put the pack on the ground to take a lens out, the front will get dirty, and not the back.
This probably confused more then helps.