In the scenario you’re describing, the “pocket battleship” option would give a situation similar to the battle involving Convoy HX-84 – but with the odds much more heavily stacked against the Germans. In the HX-84 action, the convoy only had a single auxiliary cruiser protecting it (the Jervis Bay) when it was attacked by a single pocket battleship (the Admiral Scheer). The Jervis Bay ordered his transport ships (37 of them) to scatter, then took on the Scheer single-handed to give the other vessels time to escape (which all of them did successfully). The Jervis Bay was sunk in this gallant, self-sacrificing action against an enemy which hopelessly outgunned her.
In the scenario you’re describing, I imagine the convoy commander might likewise order his ships to scatter, or might keep them together in view of the fact that (in contrast with the HX-84 action) he’d have one additional auxiliary cruiser plus six destroyers. The pocket battleship would be facing a total of eight escorts rather than one. So I think the “pocket battleship” option wouldn’t be the best choice. The “four U-boat” option sounds much better, particularly if this were in the period from 1939 to 1941 or 1942 (which is what it sounds like, given the lineup of ships you’ve described). Prior to the widespread introduction of centimetric radar around the middle of the war, British escorts were at a considerable disadvantage against U-boats when subs attacked convoys on the surface at night: the subs couldn’t be seen very well, and they were not detectable by ASDIC (which only worked against submerged U-boats) or by early long-wavelength radar (which had trouble distinguishing a surfaced U-boat from waves and other surface clutter). A single U-boat could do a lot of damage under those conditions, to say nothing of what four U-boats could do.