Are you thinking of a specific concrete 16-bit architecture where it's easy to access data objects larger than 64K?
I'd be interested to hears... I really can't. Probably the most capable architecture I'm familiar with that has a native 16-bit pointer type is the 80286, which provides 24-bit physical addressing, virtualizatoin, protections, etc. Even then, at least on Windows, key local heaps within the OS were confined to 64K, the default text editor was confined to a segment... writing image processing tools (which I did) required special handling for all but the smallest scale workloads. These all added to developer workload and reduced system capacity in unfortunate ways.
I get what you're saying that there are exceptions and hacks that make it possible to work within these limitations, but my point is that you have to care about them on 16-bit, and most of the time you really don't on 32-bit. My thesis for why that is goes back to what I was saying initially about the size of the core data types people tend to manipulate.
(And this goes back to the reason I posted in the first place, which was to explain the relative difference in motivation between the 16->32 switch and the 32->64 switch.)