It is possible for a tailpiece to have the tabs snap off for no apparent reason (it happens to me now and then, but I go through a lot of mandolins), though not typical. It is also not uncommon for a string to bind in the nut slot and snap. In this case it will snap between the nut and the tuner. With multiple E strings and two tailpieces, it is safe to assume that the E strings are being tuned too high.
We have all tuned too high and snapped a string at one time or another, so don't feel bad about that. You must not be doing too bad if you managed to change the tailpiece and get the majority of strings tuned up.
As others have stated, a tuner is great for the final tuning, but if the mandolin is way off, the tuner will have trouble until you are close to pitch. A tuner could easily misinterpret the E string and send you tuning too high.
I'll send you another tailpiece. and a couple of E strings. Once you get the new tailpiece on, I can help you tune it over the phone.
Don't let this discourage you. The mandolin is one of the more difficult instruments to deal with when it comes to tuning.
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