Been going over the next release version for Ultimate V0.80_RC3, and I believe I've corrected this issue of not having upgrades offered when they become available. One of the early issues with the game has been that when an upgrade was offered (like changing a Stern 3.50 Deck Gun for a Bow 4.50) the gun wouldn't be on the boat when the mission started. To correct this I made the guns work within a particular "date of availability", in the hope the gun would be positioned where you expect it to be. Unfortunately, when guys say they aren't getting the chance to even choose a different deck gun, we still have a problem.
With the next release, I think this has been eliminated. A bit ago someone asked when should you expect to get an upgrade? The following list contains some of the weapons and equipment upgrades and when to expect seeing them offered:
Porpoise ; Tambor ; Gar ; Gato ; Salmon ; Sargo Submarines
Air Search Radar
(SD Radar) 1941-12-01 to 1943-03-11
(Improved SD Radar) 1943-03-12 to 1944-12-31
(SV Elite Radar) 1945-01-01 to 1945-12-31
A player will be able to choose if he wishes to keep his current equipment or step up to the next upgrade.
In my tests I have been successful in getting the 5".25cal Twin Cannons onto a Porpoise after the March 3, 1945 availability date. I've been able to start a mission with a "Middle of 1942" start date (June 10th, 1942) having the 20mm Single AA as the AA gun; a 3.50 cal DG on an S-Class:
It's my belief the proper weapon will be on the sub depending when you start the Career, AND, you'll be offered the correct upgrade in-port when it becomes available.