Does calling free or delete ever release memory back to the "system"
There isn't much overhead for malloc, so you are unlikely to achieve any run-time savings. There is, however, a good reason to implement an allocator on top of malloc, and that is to be able to trace memory leaks. For example, you can free all memory allocated by the program when it exits, and then check to see if your memory allocator calls balance (i.e. same number of calls to allocate/deallocate).
For your specific implementation, there is no reason to free() since the malloc won't release to system memory and so it will only release memory back to your own allocator.
Another reason for using a custom allocator is that you may be allocating many objects of the same size (i.e you have some data structure that you are allocating a lot). You may want to maintain a separate free list for this type of object, and free/allocate only from this special list. The advantage of this is that it will avoid memory fragmentation.
It is entirely implementation dependent. On Windows VC++ programs can return memory back to the system if the corresponding memory pages contain only free'd blocks.
No.
It's actually a bad strategy for a number of reasons, so it doesn't happen --except-- as you note, there can be an exception for large allocations that can be directly made in pages.
It increases internal fragmentation and therefore can actually waste memory. (You can only return aligned pages to the OS, so pulling aligned pages out of a block will usually create two guaranteed-to-be-small blocks --smaller than a page, anyway-- to either side of the block. If this happens a lot you end up with the same total amount of usefully-allocated memory plus lots of useless small blocks.)
A kernel call is required, and kernel calls are slow, so it would slow down the program. It's much faster to just throw the block back into the heap.
Almost every program will either converge on a steady-state memory footprint or it will have an increasing footprint until exit. (Or, until near-exit.) Therefore, all the extra processing needed by a page-return mechanism would be completely wasted.
I think that you have all the information you need to answer your own question. pmap shows the memory that is currenly being used by the process. So, if you call pmap before the process achieves peak memory, then no it will not show peak memory. if you call pmap just before the process exits, then it will show peak memory for a process that does not use mmap. If the process uses mmap, then if you call pmap at the point where maximum memory is being used, it will show peak memory usage, but this point may not be at the end of the process (it could occur anywhere).
This applies only to your current system (i.e. based on the documentation you have provided for free and mmap and malloc) but as the previous poster has stated, behavior of these is implmentation dependent.