I really didn't address all your questions, so let's get to it.
First, I would thoroughly clean the whole area.
A) you don't want ANY of that 'stuff' getting into your engine (it IS surgery after all)
B) with everything clean and dry you can more easily find the leak.
Second, I would budget a whole afternoon (maybe more since it IS Solstice)
You'll need to remove the fan shroud, radiator, water pump, alternator, power steering pump, (AC compressor and smog pump if you have them)
Then the lower pulley, and using a balancer puller, the harmonic damper, spacer and keys.
Take those 4 bolts that are slopped up with orange RTV out of the oil pan, and
carefully remove the timing case itself.
DONT break one off!
Stuff a rag in the front of the oil pan and clean all the gunk and gasket from the front of the block.
Clean each part and each bolt before it goes back on.
I use Loctite PST on all bolts that go into the timing case and water jacket.
A
VERY thin smear of RTV around the water passages front and rear of the case
Third, I would definitely change the timing set, FMS, check for seal scoring and consider a Speedisleeve, check the water pump bushings + impeller, and -if you have it- the fuel pump.
Replace the coolant and possibly the radiator hoses if they have gone soft.
Jim,
Lil'Red is a '87 F250 HD, 4.10's, 1356 4x4, Zf-5, 3G, PMGR, Saginaw PS, desmogged with a Holley 80508 and Performer intake.
Too much other stuff to mention.