First, as suspected, it sounds like the credit card screw-up fault lies at least partly with CapitalOne. That is one of the reasons we stopped dealing with them a couple of decades ago. There were constant errors, but no responsibility! I also assume if you cancelled your account, there were no balances to be transferred in any case.
You refer to balances being transferred quickly, but that isn't necessarily the case. My SIL is a retired CIBC director-level IT expert, and she has assured me (with an eye-roll) that it just doesn't happen that way. Even in a highly-digital world, it is never as easy as just transferring a file from one institution to another, when they are using different systems. Priority is always assigned first to cards with the closest monthly billing date, but it still takes time to process millions of accounts. No matter how well you think the transition is set-up, there are always glitches!
In an ideal world, you and I should not have to do all the leg work to fix someone else's error. However, unless someone else magically communicates with them that an error has actually occurred, how do you expect it to be solved? It's a real pain in the *ss, but IME no one else is likely to fix it, unless they know about it! I suspect your account got transferred because you waited too long to close it.
As to the issues with the estate, let me first express my condolences, but it sounds like a problem with a specific branch, or someone who doesn't know what they are doing. I don't know where in Alberta you actually live, so a smaller, more rural branch could be the problem, especially if they lack sufficient authorization ability for larger transactions. Not usually a problem in a larger city.
What you experienced is absolutely terrible service, but it can and does happen at other institutions. I do understand your frustration and refusal to work with CIBC. I won't deal with TD for similar hassles in the past, and also CapitalOne as previously mentioned. I'm glad you found someone to finally get it fixed! There is absolutely no need to deal with someone who is either incompetent or unwilling to provide good service, whoever they may work for.
When things like that have happened to me, I have just asked it to be escalated to the manager or even to the regional director or VP. That usually has solved the problem. I am also a retired CPA, CA and CFP, so have settled a number of estates, and helped clients settle many more, including at CIBC, and have not had more issues with them than anyone else, which was my original point.
I just lost my FIL in November at 102. He dealt with CIBC in a smaller town about 100 kms. from here. The local account manager has been great in helping us pull everything together for the lawyer and getting the estate account set-up to handle the assets subject to probate. My FIL also had a TFSA with his five children the named beneficiaries.
I don't know about Alberta probate rules, but a TFSA is considered a "registered" account. Here in Ontario, a registered account with named beneficiaries does not require probate, so an estate account is not even needed. There was just a form to sign by each of the named beneficiaries, together with the signature of the executor and a notarial copy of the will and the death certificate. The funds were then released directly to the beneficiaries. We only needed the estate account for those other assets subject to probate.
Anyway, we all get frustrated at times with suppliers who seem to prioritize marketing and sales to the detriment of customer service. Don't even get me started on my recent service experiences with Rogers! My only point was that our experiences with CIBC have generally been very positive and at times exceptional.
About 15 years ago, we were in Holland, Belgium and France and discovered neither of our CIBC debit cards would work to get cash at the local ATMs with the correct system logos (and yes, we had 4-digit pins). We had put extra money into our account for our 4-week trip. They not only accepted our collect call that night to our personal banker, but she prepared and walked a bank transfer over to deposit to my RBC account across the street. The RBC debit card was working just fine! She went the extra mile and we were grateful. When we got back they never could figure out why the cards would not work. They did issue us new cards and on our next trip they worked just fine. Gremlins maybe?
In conclusion, IME it is less about the institution, although they can obviously set the tone, than it is about the actual employee or advisor, just like any business. I'm glad we haven't been subject to your experience, because I obviously might feel differently about CIBC! Hope it all works out without too much effort on your part!