Motorcycle Repair: is this mechanic going to rip me off?, bike mechanic, old bikes

Question
Hi Mike,
   I live in a pretty rural area of Massachusetts and getting your bike fixed out here is hell. Mechanics take forever and most never even show up (as they work out of their houses and get up when they feel like it). I'm done trying to fix the problem myself, since all my efforts have only made things worse.
   Anyway, after three mechanics being no-shows, I finally found a guy who is willing to look at the bike. Asking around, I heard nothing but good reveiws of him. He runs his own shop and is certified and insured.
   Immediately after he heard that my bike was an '87, he started asking me whether or not I really thought it was worth fixing. I said yes, as I had just bought the bike at the start of the season, it ran fine up until three weeks ago, and its a relatively rare model thats gotten me a lot of attention. But I agreed that anything over $500 was probably not worth fixing.
   Heres where things got fishy. He starts telling me that he wants 200 dollars in cash when he comes to pick it up. I told him I wasn't entirely comfortable with a stranger coming to pick my bike up, taking 200 dollars in cash and promising to call me. I finally got him to agree to me following him to the shop before I hand over the money, then getting an invoice with a negative 200 balance (basically an IOU until the repairs start). His excuse for this was that he had had a lot of bad experiences with people leaving their old bikes with him and then ducking out when the repairs were finished.
   I've never fronted money to a mechanic before. I may be young, and this might be my first bike, but I'm wondering whether or not to go through with this. Its getting towards the end of the season, I know, but I dont see the point of winterizing a bike that dosent run. But I guess I will if I have to.
   I told him I'd call him by Thursday to firm things up. But before I do, I'd like an opinion from someone with a lot of bike/mechanic experience.
Thanks in advance for your advice.
Harrison

Answer
Its really hard for me to say whether he is goign to rip you off or not. I do know some really small shops that charge a deposit to do work. This helps them pay for parts. You can always ask him for a few customers phone numbers that he did work for. You could call them and check his work
Good luck and happy riding
Mike