I have a classic ASP CRM that was built by a third party company. Currently, I have access to the source code and am able to make any changes required.
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Have you looked at using a memory monitoring tool to see how much memory fragmentation is happening? My guess at a possible cause is that some object of a size is trying to be created but there isn't enough room in the memory to store it as one contiguous chunk. Imagine needing room to store an object that would take 100 MB and while there may be several hundred megabytes free, the largest contiguous chunk is 90MB then this doesn't fit.
Debug Diagnostic Tool v1.1 would be a tool where Bernard's articles may help in understanding how to use the tool.
Another thought is the question of how much string concatenation is there in the code? I remember where I used to work had problems with doing a lot of string concatenation operations that sucked up memory that may be another idea to consider.
Yeah, I could see some shock at that kind of number the first few times you see it but then if you understand what the code is doing it may make sense for why so much space gets reserved right off the bat at times.
I haven't used that debug tool specifically but I did have a tool that took a snapshot of memory when pages were hung so I couldn't tell if there was a performance impact of the tool or not. Course in my case I used a similar tool in 2004 so it has been a few years since I've had to research this kind of issue.