You don't say what year you're starting on, which will make a big difference.
In 39/40 I've never had a problem getting within range of targets and their escorts; the fun and games have always been after I've hit something and aroused the interest of the destroyers.
At night I can usually manage to approach quite close running on the surface (with decks awash if you're running GWX). For the sneakier method or in daytime try running at periscope depth, silent running at 3 or 4 knots. Don't keep your periscope above water more than you need to, as that is a big giveaway. With a task force you're better taking your shot from much greater range than you would against a merchant convoy.
Later in the war escorts will be much more vigilant and radar is your greatest enemy imo.
That's my couple of pence from one comparative noob to another, though i'm sure some of the diehards will be able to give you better advice.
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