Floresta Elites said:

For question 1

i think you should go with what fits your horse and what allows you to ride at your best when looking into saddle-buying. I think saddles should be purchased after the horse is bought, so that it is properly fitted and doesn't cause sores/other problems.

About bareback riding:

i don't know of any horses that are trained only for bareback. All the horses I know are trained under saddle and can be ridden bareback every once in a while depending on how they react to the feeling of a rider directly on their back.

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question 2

boots and wraps depend on the discipline of the horse. Western is just a general category, no necessarily a discipline. Barrel racing needs overreach boots, but a western trail horse may not need boots or wraps at all. It also depends on how your horse moves and how likely it is to hit its front legs with it back ones. Of course, boots/wraps have more purposes than this.

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question 3

this depends on the horse, and what shoes it wears (if any).

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question 4

Bits depend on the horse, discipline, and rider. Hackamores aren't necessarily for beginners. There's no one bit specifically for beginners.