The place where that might be applicable (loading in a newly hostile sea zone due to DOW) would be something like the G2 DOW if the Russian cruiser moved into the same sea zone as the transport on R1.
For example, if during G1 the transport was left in SZ 114 (with the German cruiser for instance), the Russian cruiser moved in while still at peace, and there was a G2 DOW. If during G1 Germany had placed some infantry/etc. in Germany proper, then they could be loaded by a transport starting in 114 and moved to SZ 115 to land in Baltic States without combat in 114. Of course, they would have to survive any defense in SZ 114 to land the troops.
One could even do something like building a DD, a TT, and an arty/inf mix in G1 to place in 114/Germany to load in 114 on G2 and land in 115 on G2 DOW anticipating opposition from the sub and needing the DD to be able to kill the sub and reduce risk of losing the cruiser and transports.
The scenarios even for the simple above example with very few units, get surprisingly complicated with the mix of builds, placement, initial load/amphib assault, sub/destroyer/air combat limits, and the like. The sparse number of units involved mean the results of any combat are very dicey. This dicey aspect is why the early Italian/UK battles are so variable. Italy can get crushed, or it can be quite threatening based on one or two early combats.
Depending on where the Russian air moved on R1, I am not keen on the idea of moving transports to amphib assault Baltic States–a move made with the intention of securing from an R2 counterattack. If the Russians want to waste a wing of their army in the Baltic States to be defeated in detail on G3, then let them. (I am more interested in concentrating the German column in Eastern Poland threatening both routes to Moscow at once with numbers that can survive an early concentrated counterattack by Russia.) The Russian air might all be in Novgorod at the start of G2 requiring more substantial German air commitment to discourage a scramble in 115, with the possibility that the transports could still be taken out by the air on R2 since the TT’s won’t have air support and might be bereft of warships as well or be facing a sub with air with a lone cruiser depending on what happened in G2. The R2 planes can fly back to Moscow or land on a stack after such a strike.