Hello All:
In my experiences, this decisions is ultimately based on resources, time and cash flow. Working smarter then harder is something we all strive for in all our business efforts.
However, depending on your network of paysites or type of business model you may operate, (Ex: Subscription membership paysites, VOD, File Sharing Programs etc) tools/software to manage your content become necessary once you have addressed and prioritized a team's project management and the skill set of your team members.
Currently at Silvercash, we are blessed to have a solid programming team and design team that allow us to customize our content management to our needs. The challenge is that technology platforms that one would use 5 years ago becomes out dated and controlling your content dynamically becomes increasingly harder. In turn, I am confident that many of the larger affiliate programs eventually do a complete overhaul of the members' area to support this. Again, IMO, this is only an interim solution to 'get by' as growth will inherently force a team address this as competition and technology develops.
It is important to note, that many of the 'boxed' solutions are great for companies using the propreitary affiliate software, however that is mandate these software companies want you to adopt, so your investment in their product makes it harder to revisit if you want to transition your company to alternative solution. I use the example of many cell phone companies offering free hardware, but the consumer's commitment is longer to the phone service.
To reiterate many of the comments made in this thread, I believe that there is no exact 'trigger' point that company designates for automate CMS, rather it is decision based on timing and growth. 'Timing' relates to your currrent resources and 'growth' relates to a company's cash flow for custom solutions. Sometimes you have to spend money to make money
Just remember, technology is great when it works
PS: Go Leafs Go...