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I would choose b). The problem is, not only do I have the tools and facilities available to me that would make b) a relatively painless decision, but I would choose b) anyway just to get the experience from diagnosing, R&Ring, and test-driving the car myself to solve the problem.
I would not consider this "a high risk of being an unresolvable PITA problem" simply because having acess to vehicle lifts and instructors with decades of experience means that problems are unlikely to be unsolved for long. Plus, it's a conventional manual transmission - I don't consider it on the same level as trying to hunt down some drivability issue and having to go through the DIS.
If you 1) want to drive the car now 2) don't have access to what I mentioned above 3) don't want to DIY it 4) don't want to pay to have it fixed, then I would pass.
If you choose b), I would offer him $3,000, maybe less. I would probably take $3,000 because I know it can be fixed quickly.
If I were you I'd probably choose a). Why are you considering this one? Is it that good (transmission problems notwithstanding)?
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