Greetings Carla!
1. Towns are safe place, no need to roll. But you may decide as a houserule to roll instead, since it isn't in the rules, up to you.
2. Yes, the wilderness are still hostile, roll normally, nothing changes.
3. Only Healing Potions and Magic Scrolls are spendable, as is written in the card, the other items are permanent gear and need to be bought only once.
Hope I clarified all your doubts. I'm glad you enjoyed, thank you very much for playing and for the feedback!