Does anyone know if money allocated for medical expenses (pre-tax) is lost if you don't use it up in the instance where you are hired by another company... or can you get some of it back??? Any insight would be appreciated

You can't get it back unless you put in a claim for expenses incurred during the time of employment. BUT (from my HR Director wife):

1. You can put in a claim for the entire amount elected. So, if you elected $1200 for the year ($100 per month) and left in January, you can put in a claim for $1200 even though you only contributed $100 (or perhaps less).

2. You can COBRA it. So, in the first example, you can elect COBRA for February, pay $102 (the 2% administrative fee) and spend $1200 in Feb.