1. Orbitting moon? It can orbit asteroid/structure/npc ship. Bookmarks created automatically. You need to define proper anomaly bookmark name to be second in people and places (first is station) when bot create it. Yes bot may bookmark completed anomaly in shared folder. Check
manual
2. Looter can visit and loot bookmarks created by hunt bot. It does not use mtu, only tractors and salvagers. When bookmark is cleared it will delete bookmark.
VMware may be used but I don't officially support it. You need to know how to make properly working vmware vm. I would recommend
vm15, 1 CPU, 1 Core, 500Mb graphic memory, 3Gb memory, 250 Gb disk (not preallocated), windows 7 64bit original trial version.
1 character means one eve client window. If you want to use bot with 2 different accounts at the same time you need 2 licenses.