Only you can answer; but maybe you don't want to know. Ignorance is bliss so they say, and in this instance, it may be best to simply enjoy a state of blissfulness.
What might be more important than having gotten a bargain or having paid too much in the past, is how best to shop for your next saddle.
Today's "using" saddles can be priced from several hundred dollars to more than $8,500...and specialty or antique saddles can easily range into the tens of thousands.
The keys to a perfect saddle purchase are: value, fit, fit and fit.
Value is paying a fair price for the saddle, and a fair price can be defined as "exchanged worth." You are going to give so many dollars and you want the saddle to be an "equal exchange" for those dollars. So it's a matter of perception...if dollars don't mean much...then the number of dollars you pay doesn't mean much. On the other hand, if dollars mean something, you better be getting your money's worth.
When you decide to buy a saddle you are saying, "I want this particular desire fulfilled." You need to be pretty well focused on what that desire is, and what can fulfill it. No wishy-washy idea will do.
Know the kind of saddle you want!
To help you identify and fulfill your desire, three things are mandatory: fit, fit and fit.
The saddle must fit you! English or western, jumping or cutting, pleasure or gaming, you must be comfortable in the saddle at all times, all the time. A saddle that makes you think about it when you are riding is overpriced at any price. When you are riding, your saddle should be so comfortable that you never think about it.
No matter the price, you've paid too much if the saddle doesn't fit your horse. If you are buying a ready-made saddle, you must have the opportunity to "try it-on your horse-before you buy it." If you can't do that, the saddle is no bargain. (If the saddle is being shipped from a far away maker, then you should have the right to return it if it doesn't fit the horse...be reasonable...you don't need to ride the horse more than a few minutes to determine fit.)
If the saddle is custom built, the saddle maker will want measurement of your horse in order to determine the proper tree, skirt lengths, gullet, etc.
Finally, the price must fit your budget. It doesn't matter if you can spend $1 million on a saddle-set a budget so you'll get a saddle that satisfies your definition of "value."
Here are a couple of "save dollars" shopping tips: if you are ordering a custom built saddle, tell the saddle maker the highest amount you'll pay, and then let him design to fit the budget. Saddle makers can be very creative and stay within the budget...see the design, then decide. If the design doesn't thrill you, shop another saddle maker.
Buying a used saddle that fits, fits and fits, plus is eye-appealing to you is often a better value than getting a new saddle.
When it comes to silver, more is less. If you are buying custom only have "sterling" silver used; silver plate and other imitations fade fast and are dollars wasted.
You can get what you want at a price you are willing to pay, and it will be a bargain if it fits, fits and fits.
If it doesn't fit three ways, you've paid too much!