Re: SIX MONTH OLD ITCHY SITUATION
I also had a little stray who ended up becoming and indoor/outdoor cat. He was sadly hit by a car in the end, but he was living with me and my boyfriend for about five months or so, during one of the hardest winters my state has ever seen.
He still wanted to go outside, even with the ice and snow. He'd actually leap up, dig his claws into this little key holder we have hanging from the front door knob, and hang there, yowling, until we opened the door when he decided it was time to go out. XD And still, through the freezing weather and barren conditions, when he came back inside he gave us fleas.
Advantage worked great for him, but I'd personally recommend using a flea treatment year round, from my experience. Especially if you live somewhere that doesn't get the hardest of winters.
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Silas-Male Ginger Tabby