Quicken Premier 2018 R.9.30
Build 27.1.9.30
Windows 10
I've found some weird behavior which makes it very frustrating to review downloaded transactions: sometimes Quicken fails to update downloaded payee names to what I've set in renaming rules or to properly categorize transactions. Matching transactions is also really un-intuitive, so I'm not sure if I'm doing something wrong, or this is just another case of Quicken not working (I also have the problem where shortcut keys don't work and some transactions just don't download but those are separate issues y a a a a y).
Here you can see my renaming rules for one of my credit cards:

Here's where you can see that Quicken doesn't seem to care what I want:

Do my rules not cover these two situations? I've verified I don't have any other rules regarding Citi at all, so I don't see what if anything would be conflicting and causing this behavior.
I have a payee which receives 3 different categories of payments each month and the amounts are fixed. I
thought I could use Memorized Payees to essentially tell Quicken "when you see a transaction from this payee for this amount, assign it this category". When I update transactions and review them, however, Quicken assigns each of these transactions to whatever of these 3 categories it likes the most.

Does matching even work? Manual matching has no search function (which is an interesting design choice) and I can't use it to find existing transactions--they don't seem to be found by the manual match function.
You can clearly see the downloaded transaction matches the one already in the register:

but if I try to match it manually (Quicken cannot find this on its own, for some reason), here are my options:

The transaction from the same date, with same payee and same amount is conspicuously absent as an option to match this downloaded transaction. What am I missing here?
I appreciate anyone's time and effort who takes a look at this and has any input. This software has me ready to pull out my hair.