My two year old has started his ground work with a saddle on and the saddles I have sit on his withers so bad that the back of the saddle is actually popped up off his back. My dressage saddle does the same thing, obviously I need a saddle that can accomodate higher withers. Once he's been in consistent work (5ish) I plan on getting a custom made saddle for him and me.

My first option is http://www.idealsaddle.com/catalogue/sad ... My trainer is selling it used, it's in good shape, she wants around $ 800 for it. It has clearance for his withers, seems to fit him okay but once he starts working it's not going to fit him anymore. The saddle can be reflocked but obviously it's a fixed tree. It's all leather, very high quality, etc. Very, VERY cushy in soft.

My second option would be to go with a Thorowgood Dressage saddle, they have their standard which is for a "medium wither" horse or high wither for high withered horses. http://www.thorowgood .com/types.html He looks like the horse in the middle but where he's still growing he could pop up, so obviously I need to figure out which one fits HIM the best. The saddle is synthetic, a couple hundred dollars less than the one my trainer is selling and adjustable. I have no issue with synthetic saddles but I know from personal experience they don't sell used for an awful lot.

pets question and answers,www.5d2d.com

I haven't actually SAT in either one of these saddles yet, which will obviously make a little bit of a difference but my primary concern is fitting my horse the best for the longest period of time.

I think you should get the saddle that both fits your budget, include the cost of re flocking, and that you are most comfortable in. Both saddles will work with your horse (is one works and one does not go with the one that does) it is just a matter of how you want to go about getting it done

I would recommend buying a foam wither pad. It will be both cheaper, and just as effective if not more, than buying a new saddle for him, especially when his frame and muscling are going to change as he is worked with more.

Here are some potentials:
http://www.doversaddlery.com/product . asp? pn=X1-1905 & tid=froogle & CATALOG_CODE=1X814 & EID=X1814001 & zmam=1460880 & zmas=1 & zmac=49 & zmap=X1-1905 & bhcd2=1283704930

http://www.doversaddlery.com/rider% 92s-international-half-pad/p/X1-19567/cn/1405/

http://www.doversaddlery.com/roma-wither-relief- lift-front-half-pad/p/X1-19456/cn/1405/

Riding for 11 + years and working around horses for longer than that .

Though I cant really tell you what saddle you should buy out of those 2 in particular, my best advice for your high whithered horse would be to find something that fits relatively will but also purchase a high quality, sheepskin whither pad ...
I have a very high whithered horse myself, and I ended up buying a bates close contact saddle with an interchangeable tree.
The saddle fits very well almost everywhere but his whither still knocks at the pommel. We bought a hefty sheep skin whither pad (about $ 150 dollars) and I haven't had a problem in over 6 years!

Hope that helps!

(Bates also makes dressage saddles with interchangeable trees)