Even when unchecking the historical U-boat availability dates in SH3 Commander your unable to get a Type IX in the 2nd Flotilla until Dec 39.
Here's a quick workaround:
Go into the Data\Cfg file, open up the Basic file, scroll down to the area below and change the value 12 to 8 (in yellow bold for illustration purposes).
[SUBMARINE2]
NrMinOff=3
NrMaxOff=5
NrMinPO=10
NrMaxPO=19
NrMinSeamen=24
NrMaxSeamen=32
NbVersion=4; 5
Version0=0 ; IXB
Name0=IXB
Month0=12 >
8
Year0=1939
Version1=1 ; IXC
Name1=IXC
Month1=7
Year1=1941
Version2=2 ; IXC/40
Name2=IXC/40
Month2=10
Year2=1942
Version3=3 ; IXD2
Name3=IXD2
Month3=1
Year3=1943
;Version3=3 ; IXD1
;Name3=IXD1
;Month3=10
;Year3=1941
;Version4=4 ; IXD2
;Name4=IXD2
;Month4=1
;Year4=1943
DaysSpentInBase=28
Save the changes then boot up the game starting a new career commencing August 39 in 2nd flotilla.
Sail around the harbour in your Type VII for a few hours then save the game.
Go to your SH3 folder in C\MyDocs and go to the career save and change the Delta Renown (I changed mine to 50000.00.
Save the changes then boot up the game, go to the upgrade screen (see below) and purchase a Type IX for 9000 renown (leaving you with a healthy 41000).
There is another method of making the Type IX available but that entails opening up a lot more files and running the risk of your installation becoming FUBAR.