genia, I don't think you are being cruel. It sounds like you've done more than enough and should give yourself more credits.
The question is, what will you offer as the substitute to the breast and how long can you tolerate frequent middle-of-the-night cryings. I think, depending on the substitute to the breast you plan to offer, you could end up being much more tired than feeding him in bed because he will still wake up the same number of times until he has learned to put himself to sleep without your help.
For us, when we tried to night wean her the first time the only substitute dd took was one of us (mostly dh because with me she'll want breast) holding her almost upright (many times accompanied by patting/singing). It was very difficult because dh ended up holding her almost all night. And she seemed to not sleep well and wake up more often too. We gave up after several nights because she seemed so miserable with the sudden change and we just couldn't hold her all night long for many nights in a row. Our strategy at that time was to hold off BF as long as we could without her screaming too much. I think that didn't work well because she ended up being both hungry and tired and didn't sleep well as a result, ie she fell asleep because she was too tired but couldn't sleep well because she still felt hungry (out of habit, but nonetheless hungry) and woke up again very soon.
Anyway, my new (current) strategy is to give her scheduled feeds, like at least 3-4 hours apart for 5-10 min at the most each time, just like what she can manage when she's awake. So now I know she shouldn't be hungry in between those scheduled feedings and get dh to hold her or try to hold her / cuddle her myself. Also I assume she's not hungry because my breasts don't get so full even though I don't feed her at 2 hours after the last feed like before. But if I wait for 5-6 hours, my breasts will be quite full. I think this is easier for her and for us. And hopefully we can space out the feedings more and more and try to feed less and less each time too.
My experience is like what mears said. It is very difficult for her and for me to sleep with her and not feed her. If she sees me in the room (since she's young enough to not know it I can sometimes hide under the duvet), she'll want me. And if she gets to me, she'll want the breast.
And many many times in the middle of the night (no matter what strategy I decided upon during the day) I just wanted to go back to sleep and decided to feed her because it's quick and easy.
So as much as I hated to, I tried putting her in the cot. Some nights it got better, she woke up less (4-5 times compared to 6-7) but other nights she just didn't let us put her there and we had to go back to bf her in bed again. But it was definitely much easier to get her to accept a holding instead of a feeding when she slept in the cot.
We also plan on sleeping with her for a while longer now, so we're working toward getting her to accept a cuddle or just our presence to go back to sleep.