I completely sympathize, and I've been banging my head against a huge brick wall for months at the Wednesday Board Hours trying to impress upon them that this is a far larger problem for Canadian sellers than eBay.ca staffers believe (or at least claim).
You are right that this issue is yet another hardship and handicap for Canadian sellers (as if we didn't already have enough challenges vis-à-vis our American counterparts. The "cart disconnect" has been ruining my ability to make multiple sales (and unfortunately the majority of my items are the type that used to attract a lot of multiple orders before the whole cart mess began). It's probably also losing me a lot of frustrated buyers that I will never hear from or know about.
Now the eBay.ca staffers claim that the eBay.ca cart functions perfectly if one is logged onto .ca. However, my tests have shown there are problems even there. The situation #1 you describe may be yet another sign that things aren't functioning correctly even within .ca.
Some time ago I put up the notice which you'll see on my storefront page, asking buyers to log onto .ca or contact me if they're having any problems checking out. However, I frankly think U.S. buyers will be reluctant to sign onto a site other than .com, and the rest just won't bother to ask me to help them.
The "Immediate Payment Required" for items under $1,000 (I believe that's the ceiling if I recall correctly) has, to my understanding, been in effect for about a year, and as you say, it can be a serious problem-maker that just adds another layer of complexity and dysfunction to the already badly broken cart system.
Apparently IPR was the final blow in the "disconnect" between the US and Canadian carts, but who really knows whether it may also be affecting the .ca checkout system? The scenario #2 you mention really should not have happened if your items were all listed on .ca, and you didn't have IPR on them.
There are two factors involved which I think are influencing eBay's reluctance to do anything about this problem:
1) It's almost exclusively a problem for Canadian sellers (for the reason that I would think most of us have a large U.S. buyer base who shop on .com). Accordingly, or so we're told, eBay headquarters in the U.S. has virtually no interest in making our little problems their priority;
2) EBay is making money (in FVFs on shipping) from every Canadian seller every time a .com buyer can't make a combined multiple order using the .com cart in order to get the seller's shipping discounts, and ends up purchasing all the items individually. In most cases, honest sellers will refund the excess shipping to the buyer (at least I do), but in the meantime eBay has already collected all the FVFs on the individual items' shipping costs. This may amount to only a dollar or two per occurrence, but multiply that by the thousands of times this problem likely occurs every day, and eBay is raking in a lot of free money from Canadian sellers. Why kill the cash cow?
I'm sorry if I sound rather bitter and cynical about this issue, but frankly I've come to the point where I've realized there is almost nothing I can do about it except hold out a meager hope that it may get fixed someday (or else list on .com, which for many legitimate reasons I do not want to do).
It's a very sad and disgusting situation for an online selling venue as big and powerful in the marketplace as eBay is to make it so difficult for buyers to simply choose what they want and pay for it, simply, quickly and easily. For some reason, other online venues have been able to figure this out.
You are absolutely right that buyers are not going to want to have to do "workarounds" or go through complicated steps to checkout and pay. That's a huge problem for Canadian sellers, and I would think it should also be a concern for eBay HQ because every buyer who gets fed up trying to choose and pay for his items may just decide to give up on eBay completely.
Of course, if you're inclined toward conspiracy theories, you could not imagine a better way to finally deliver the coup de grâce to Canadian sellers in order to encourage them to migrate to .com (and perhaps close down .ca forever?). Oh, but I'm looking for logical motives in eBay -- I forget that they are quite capable of being just plain stupid. 
Sorry for the vent too, but this subject really isn't funny anymore.
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