@vandefiets @bert_hubert @tinmouth @vosje62 @jwcph You've got layered issues with most corps.
1). Cost of switching (the CFO cares about this, and the CIO saving in the budget potentially). Liicensing is mostly what I mean here.
2). Training users and IT staffing
3) integration of existing tools, this includes management tools and monitoring and also LOB apps
4). Regulatory requirements. This can be burdensome for self hosted tools if staffing or compliance has shortages (most mid orgs do).
5). Supply chain integration, this includes sharing of documents, repositories, and automation
6). Tool switching friction, especially for C suite. Email is a huge example, I could talk to this for hours.
7). Juniors and seniors friction in support staff, this is a huge challenge in all potential migrations. Seniors may want to adopt a tool, as it's well adopted for senior skilled staff, but juniors do most of the day to day work in that tool, I've seen so many migrations fail due to this.
8). Vendor support. Open source projects can be huge challenges because so many times the expectations are, We are short staffed, we have a maintenance contract, open a ticket. Self supported can make this a challenge
Migrations a nightmare for any mid to large org, again, if it's not driven or adopted from the top, the beast we know is better. It's why MS and others push so hard for long term contracts and offer such a large discounts for those who do, that lock in is the goal