I think what we haven't really gotten down to is that the 360 and the F430 are reasonably different to drive. If you're on the fence between the two, and you're concerned about maintenance costs (which are generally higher for a Ferrari, regardless of the model, than your usual M-B cars), then test drive both of them and see what speaks to you. Maybe then we can give you a better idea of the maintenance costs. We can say all day long that F430 maintenance costs are lower than 360's, it's pretty much fact. But the magnitude of the difference is up for debate. Also, we don't know your personal feelings on the larger up front cost of an F430, versus the down-the-road incremental cost increases for operating a 360. Think about how much maintenance you can buy for the $100k difference you have stated. If people are advising you to set aside $2k per month, and your term is 10 years, you're in for $20k maintenance, leaving $80k remaining (savings) from the acquisition cost difference. This is a very simple calculation - there are many other excluded variables!
I bought a 2001 360 Spider F1 - so right up "problem alley" according to Brian (he is a respected Ferrari mechanic). However, and lucky for me, my car has an excellent top operation (as of now) and a great F1 system history (again, as of now). Totally agree that fixed top 6 speeds are generally lower maintenance costs. But, I wanted a Spider and F1 gearbox, and I can pay for those today and to repair them down the road, so I did. I haven't looked back.
I also have to think about belt replacements - oh well, so be it. After I bought my car, I sank almost $25k USD in various repairs, enhancements, and improvements. I'm fine with that - the money went a long way towards buying problem-free miles. High-ticket items included all four brakes, new exhaust headers, new exhaust cats, a paint correction and interior detailing, installation of a rear challenge grill, and replacement of all eight intake manifold gaskets. These cars aren't problem free, and problems are expensive to fix. Fortunately, that's all it takes - throw money at it and you have your result, so it's easy.
I would seriously advise the test drive in both before you try to figure out which one is the right car based on operating costs. Buying your first Ferrari is as much an emotional decision as it is a comparison of dollars and cents. Bottom line, know what you want - find it, and go in with your eyes wide open. That process took me 1 year.
Edit: PS I love Hong Kong! Did some business with the Jardines Group several years ago.