Savannah knows my bed as 'the bed' which is why I just put her there all the time - day and early evening. I find if I put her down right as she is falling asleep and offer her the boob she'll drift off after a minute or so. I'm the same as you - I go in and offer it again when she stirs.
She's been in there from 7pm the past week and a half, right up until I go to bed around 11pm - midnight. I have a mini mattress protector with one of her blankets on top of that, and that's where she sleeps. Makes it really handy to grab that and slide her across to change feeding sides if I need. Also because I leak everywhere, and in case her nappy leaks, I don't have to change the whole bed.
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