Will it hold 4, 750ml bottles?

Yes, I even put 3 750 and one 1.5 liter

Will this fit 2 magnum bottles? 1.75 ml bottles each?

It ia a great insulated bag but I'm pretty sure would not fit a 1.75 ml bottle height would be fine for 1

Would 8 of their insulated wine glasses fit with2 bottles of wine

I'm not sure what is meant by "their insulated wine glasses" but I have carried 2 bottles of wine and two large Riedel glasses. I've also fit two metal insulated cups (10oz Ozark, non stackable) in one of the wine compartments with a couple bottles of sangria. So depending on their size/width and if they're stackable you may fit some. Not sure about 8

Tirrinia 4ボトルワインギフトキャリア – 断熱&パッド入りポータブル万能ワインキャリークーラートートバッグ 旅行/BYOBレストラン/ワインテイスティング/パーティーに ワイン愛好家へのギフトに最適 ブラックストライプ

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Tirrinia 4ボトルワインギフトキャリア – 断熱&パッド入りポータブル万能ワインキャリークーラートートバッグ旅行/BYOBレストラン/ワインテイスティング/パーティーにワイン愛好家へのギフトに最適ブラックストライプ