Of course it hurts. We are human. We try to do the best we can and help those in need. You have made a very difficult decision, but you saw that it needed to be made. I am so sorry it came to this. Thank goodness you made this decision before any of them suffered any serious, major illness, which you could not afford! That is a good thing. And oh how I know how hard it is to sort out who is ill when you have multiples. I had to do that once w/ a UTI and 'someone' peeing outside the box. Took me 2 days to sort it out and then the darn vet (not my vet) told me off for letting the kitty suffer for the extra 2 days. Geesh! We in rescue don't need that, we already know! We see it, we feel it, we struggle with it.
I'm glad that Rory is on the mend now. He will feel better soon!
I don't know about the other three, but re Rory, Reece and Radar, do mention if you think any of them are bonded and should be kept together if at all possible. Makes the change less stressful for them, if they can remain with a bonded pal. I think 2 of them came in together and may be bonded? You will know.
Making hard decisions hurts. If it didn't hurt, it wouldn't be hard. Sending you cyber hugs as you go through the transition.
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