*****UPDATE*****
So my wife got her work bonus recently and said "just let the dealer take care of it on me". Well that's great but I still don't want her wasting any more $$$$ than necessary so we made a cutoff of around $1k. It went in for an estimate and things got annoying real quick. First the charge for the estimate went from $90 to $125 (pick up/drop off was $50 of that). They spent a full hour cleaning and looking at the drips and determined exactly what I told them. "It's leaking from around here somewhere". Thanks.
Then the estimate for the repair went from $900 to $1220. My favorite part is that they think it is just the gasket but it may be a plate behind the hydro pump. If that plate is the issue then that tacks $900+ to the bill.
I understand that the dealer has to make $$$$ and that sometimes you don't know what a problem is until you get into a project but for some reason the whole situation just bugs me so I'm just getting the tractor dropped off back home, I'll order a manual and take care if it myself in the Fall when there is less tractor need. I have a few ideas for interim fixes and I'll update as I give those a shot.