A new OEM starter goes for
$300 online - ouch. RockAuto sells remanufactured starters only, and I doubt any chain stores sell new ones. Maybe if you get a reman one from a reputable brand (Bosch, Beck/Arnley, etc) it might be fine, not sure. Have you checked both ends of the battery terminals for corrosion or damage, and had the battery tested to rule it out?
Did your mechanic check the transmission fluid with the engine idling, and after selecting every gear and returning to P? If not, he checked it incorrectly. I'm unsure of the approximate cost of a pan drop & filter change and fluid exchange, sorry. If you are up to it, you can do a pan drop & filter change and fluid exchange in your driveway. There is a DIY guide on the pan drop
here, and fluid exchange steps are in the
general information thread under the "Transmission & driveline" Q&A section.
I'd imagine the cost of headgasket replacement to be quite high as it's difficult to access and might require removal of the engine (at least the factory service manual recommends it).
I think you should ask around for an approximate cost of head gasket replacement and then weigh your options from there. You can likely DIY the starter & transmission service, so you'd just be paying for the head gasket work. Maybe get another opinion about the head gasket too, I still find it odd to hear of a head gasket issue with our vehicles, especially if you're pretty sure that it never overheated. Has it ever had a coolant service?