shoing isn't necessary unless you'll be cart driving on the roads which wears horses feet down, which I'm sure isn't in your agenda.
This isn't necessarily true. There are some horses that are just tenderfooted and need to be shod all the time. My friend's arab gelding is one. Pull his shoes off and he's almost instantly "lame." My other friend has a OTTB gelding who won't even walk on grass without being shod. Other horses, like my Aires, could care less and will go over pretty much anything you ask them to completely unshod. My BO recommends all the horses at our barn be shod to ride up the mountain (Granite Mountain in Northern Arizona...lots of boulders, rocks, etc). He keeps all his horses shod so he doesn't have to worry about them being ouchy on the rocks or slipping (some of them are older and not as sure-footed as they once were).
So, I would say talk to your farrier about shoeing. They'll be able to give you a better idea of how strong your horse's hooves are and if they'd likely need to be shod. I asked my farrier if he thought Aires would need to be shod and he said "Probably not because of how tough his hooves are, but you won't know until you try him on some trails."
Again, feeding is a personal preference. My horse gets about two flakes of alfalfa morning and night (he's two and still growing) and he is at a healthy weight with a super shiny coat. Some people would say that he needs supplements and grain and such. Maybe when he's a little older and we get into harder work, yes, he'll get grain. As it is, he's worked three or four times a week lightly and we're going to be doing light trails once, maybe twice a week, so I don't feel he needs the extra calories. I would talk to your vet and see what your vet thinks would be a good feeding routine for Crescent.
Saddles I can't help with, as my preference for a pleasure saddle runs more toward Aussie saddles and I'll eventually be doing English with Aires (want to do eventing). Just make sure you buy for quality, not just looks. I know a lot of cheap saddles may look good (especially the cheap ones with the "ostrich" leather seats), but they won't stand up to much use and abuse. Buying used is probably the best idea, unless you're going to be doing higher-level shows. I got my nice Aussie saddle for $125 from a local tack consignment shop and my bridle from eBay for $37 including shipping (bridle isn't used, but I had to order online because Aires has such a big head).