It all depends on the mods loaded, difficulty settings and the year of the war.
Early war the escorts are not very good but the torpedoes are very cranky (especially with the HSie mod installed) so you want fairly calm seas. All the torpedoes malfunction a lot in rough seas at the shallow settings needed for impact detonations. The early electrics have very unreliable magnetic fuses as well, so they are pretty useless in rough weather. In 1939/40 I tend to shadow the target until the weather improves.
Folks who use the super auto targeting from the weapons officer like to sink all the escorts then wipe out the convoy with the deck gun. This requires calm seas <7m/s. I can't see how this is possible with manual targeting.
Late war (1942 onwards) the escorts have radar, long range/wide angle ASDIC and excellent passive sonar. All these are degraded by rough weather. All the merchantmen are armed and the deck gun becomes very risky. However the torpedoes are much more reliable, especially if you set them for magnetic detonation to run 0.5m under the target. So you want some waves. 15m/s is still tricky.
Night surface attacks are very possible up to early 1941, but I find it hard to keep track of where the escorts are unless I turn on the map icons and I've never dared to actually go right into the convoy. This progressively becomes very risky from mid 1941 as merchants get armament and escorts get radar. All the great early war uboat aces attacked on the surface, and sailed right into the convoy, but many of them were lost in 1941.
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