You get the picture. And I know you have had the plants. And the challenges. And the losses. I have absolutely no idea how many plants I've killed over the years, but I am quite sure it is hundreds, if not thousands. (Not including annuals, or even houseplants!)
However, although my new garden is much smaller than my former one, and so I have to be selective about what I choose to plant, (and do a lot of containers). But there are certain plants that I just enjoy so much, even though they may not come back for me, that I just have to have them if they can be purchased for just a few dollars. There IS one exception in this list, but you'll see it when we get there.
We'll start with Primula capitata 'Noverna Dark Blue'. (left photo) I decided mine had NOT come back, so I bought another one. But what surprised me was that Primula vialii (right photo) survived the winter and has returned. So you really do never know.
Plant breeders are getting smarter about their new releases that aren't so hardy. That's the case with a number of coreopsis cultivars. Remember Limerock Ruby? We all loved it when it came out and it was listed as being zone 5...not on this planet! (it's now listed as zone 8). Well...the breeders are now marketing some of these less hardy varieties as annuals, and I picked up two of them: Cherry Pie and Pumpkin Pie, both for 4 dollars each. They are extremely floriferous, I have them planted in windowboxes and in my cutting area, and once they are done, they may go to sleep. I DO have Mercury Rising, from the Big Bang series, overwintered and growing well in an excellent drainage area, so maybe I'll try one of the other iffy varieties near it.
This is the blue-flowered plant you might have noticed in the previous photo. It's not an ice plant, but a relative of pulmonaria and borage, Lithadora, or blue lithospermum. However, it's cranky about overwintering, again because it wants a welldrained location--and it also wants acidic soil, like rhododrendrons, heaths and heathers. So I have it planted in a cinderblock and we'll see whether it survives or not. I genuinely am okay with it just enjoying its summer and then going to sleep, but I know other gardeners in Nova Scotia who have had it overwinter, so why not give it a try, says I?
This is another relative of lithadora and pulmonaria, Anchusa 'Lodden Royalist' also called bugloss (one of numerous plants with that common name) or blue alkanet. I have never been able to get it to overwinter OR to self-sow, and it often just dies away towards the end of the summer, but I still look for it every year so as to enjoy those rich blue flowers. If it has blue flowers, I will make all kinds of excuses to justify having it. We know that.
So the moral of this long meandering post is, if you enjoy plants but they are supposedly divas, try them anyway if you can easily source them and they aren't expensive. You'll get a season of bloom from them, as we do our annuals, and they might surprise you, too.
Except yellow hollyhocks. I have finally given up on those.