The Pines translation is the best. Better than the ibn Tibbon translation by far. Unless you are history scholar, there is no reason to ever need to read this version. If you want to study it in Hebrew, the only edition worth reading is the Qafih edition. That's actually true of any of the rambam's works.
The best place to start is where the rambam says, not with the guide. If you sit down with the guide without any experience in secular philosophy, you're just plain doing it wrong. The guide was written for the student of philosophy who has difficulty with Judaism, not vice versa. And religious Jews are frequently surprised that a book about metaphysics and philosophy doesn't teach you anything about metaphysics and philosophy. This is why the overwhelming majority of those who have studied the guide didn't understand it.
Before you sit down with the guide, you need a thorough understanding of philosophy as it was understood in medieval Islamdom. Primarily that means Aristotle. You must have an intuitive understanding of Actuality and Potentiality, the Four Causes, and Islamic philosophy of mind with an emphasis on intellect. You must learn to think in these terms as the guide is explicitly written for "one who is inclined to think in a certain way." You will not find this information in any book written solely for the Jewish audience unfortunately. You will need to branch out to secular academia.
He also assumes familiarity with his earlier works, the Mishneh Torah and his commentary to the mishnah. In my experience, you can get by with just the introduction, pre-chapter introductions, and shemoneh peraqim and the commentary to pirkei avoth. This is of course in addition to Tanakh, Talmud, and the midhrashim. However, the Pines edition is well footnoted so you can investigate as you go along.
My last piece of advice is to go exceedingly slowly. Contrary to popular perception, the rambam is not obtuse or hard to understand. If you aren't understanding what he's talking about, it means you haven't done your homework. Put the book down and study the requisite philosophy and rabbinic texts until you are ready to try again. My first reading of the book took three years as I had to go back and revisit the philosophy to understand it. My next reading went much easier because I had developed a personal relationship to philosophy that the rambam was directly addressing.