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@K.Coo
I'm in a very similar situation and have been wondering about asking here for advice for a while.
We live in a first floor flat with Bella, who's 5 and has previously been a very outdoors cat. We'd like to let her out, also through two front doors: when we moved a couple of months ago we kept her in for a few weeks until she chilled out, then she started appearing really keen to explore beyond the front door. We let her out one the morning hoping she'd be around when we got back: no sign, cue panic. She was mewling pathetically in our neighbour's back garden (she'd got round to the back of the terrace and apparently forgotten how to get back round the front). We had to go and ask our neighbour if we could retrieve her: she stank like a fox and we basically had a big fight with her in his garden then his living room/ kitchen/ bathroom (she hates being picked up). She recovered from the ordeal (as did we, eventually) and is now quite miserable again, clearly wants to go outside. But what if she can't find her way back again, again? And she has to be here when we get in as we can't leave the door/ window open.