Let me make a remark from a MerC Alpha owner's perspective: MerC usually has an Exhaust BELLOWS, and it connects from the Transom Assembly to the Outdrive. When the Drive is in Trailer position, both ends are connected. But MerC also offers an Exhaust TUBE, which connects only at the Transom end. In Trailer, a GAP will show.
So... does Volvo Penta do the same thing? If you're seeing the gap with the drives RAISED, could be it has Tubes and not Bellows.
That said, I don't think exhaust bellows or tubes are behind your stalling problem. The MerC Alpha has a cutout switch to help get the drive out of gear going to Neutral. If you had those drives, I'd say look for a sticky Lower Shift Cable. The one from the engine down to the inner transom assembly, but to my knowledge no VP uses the Switch.
It's not a good idea to back any I/O down hard. Risks forcing water up the exhaust to the engine. VP and MerC both had "Shutters" in the top of the Y-Pipe to offer some protection against that. Same idea as the rubber flaps you see over some inboard exhausts at the transom. VP came out recommending removing the Shutters. MerC still wants them in place and I always replace them. I towed a disabled bowrider with a VP that seemed to be waterlogged. They had anchored from both ends with the stern toward a light chop and a lot of boat traffic. My thought is that water was forced in through the exhaust. Leave Shutters out if you want, but please don't back hard or anchor stern to the weather.