Forget category c: some things are truly disposable and can't be reused in their current state unless you want to start a recycling company.
Category B is the most interesting. For tools, there's eBay: just resell stuff you don't need. Even then, a lot of what we do is specialty stuff: I have 6805J programmers that no one wants even for the cost of shipping. They've simply outlasted their usefulness.
The problem with reusing hardware is the documentation has to be perfect, or the time spent trying to reuse a board or other hardware becomes more costly than simply starting from scratch again. I find that for the things I build for other people, I'm pretty good at keeping good documents. But for stuff I build intending to use for few days and then forget about, documentation is pretty much none existent, so boards end up permanently consigned to the junk bin.
I haven't worked on anything that needed a 30-year product life, but I have worked on products that went into semiconductor manufacturing equipment, and needed 10+ years of support.
At least in those cases our customer was sane enough to realize that sometimes a slight redesign is the most cost effective and reliable solution.
Not every semiconductor manufacturer does lifetime buy notifications by package
Every reputable semiconductor manufacturer will give notifications on a per-part-number basis. If there is a manufacturer out there who doesn't do this, I wouldn't purchase from them for any project, let alone one with your stringent support requirements.
Reputable manufacturers don't just notify if a part/package is going obsolete, they notify for any change in the product that might impact quality (in the ISO 9000 sense). For example, they notify if the lead finish is changing from tin-lead to matte tin. They notify if the device packaging process is being moved from one factory to another.
some manufacturers simply fold up and disappear
This, or course can't be helped. And there are other similar risks.
David mentioned a case where a factory fire resulted in product obsolesences without notice. In another recent case I know, a (large and extremely well-known) fabless semiconductor company was forced to obsolete several lines of products because their foundry vendor decided to close down an older (and no longer sufficiently profitable) manufacturing line. At least in this case they were able to give advanced notice and allow for lifetime buys...but their products were not $0.05 transistors, they were complex $20 - $200 ICs, so you can imagine the investment required for some lifetime buys.
Other risks -- regulation
One more thing to watch out for is the march of environmental regulation. The European RoHS directive and similar laws may not apply to your products, but they affect your supply chain. RoHS, for example, forced a lot of mature products to be redesigned, reducing sales volume for a lot of mature components, which probably resulted in some obsolesences as specific parts became unprofitable.
New versions of RoHS are expected within a few years. So you can expect a new wave of obsolesences as the market settles out in relation to the new rules.
Other risks -- changed market landscape
If you designed a product 30 years ago and you designed it entirely with multi-sourced components like 2N2904's and 74LS04's, you would very likely still be able to get all those parts today.
But the trend in the last many years is away from multi-sourced components. Very few new products are being replicated across manufacturers. And the parts that are are at similar complexity levels to what was available 30 years ago --- hex logic gates, individual transistors, etc. Even "simple" devices like linear power regulators are now complex enough that nobody tries to duplicate another company's design exactly.
If you want to design in a microprocessor or a programmable logic device, you are simply stuck with a single-source component, and all the risk for long term support that entails.
Also, as my anecdote above pointed out, the rise of the fabless semiconductor company also adds risk because it means your chip vendors may not actually control their own manufacturing resources.
Strategy
To me, it sounds as if your sales team needs to get tougher with this customer (of course, engineers always say this).
One option is tell them you can fix the problem their way, but to maintain this level of support, the product price will be increasing XX% each year for the remainder of the product lifetime. You can make a lifetime buy for these obsolete products, but you'll need to pay for engineering evaluation of the requirements, technicians to manage the inventoried parts, etc., and you need revenue from these products to support that.
Another is to call their bluff on the re-tender process --- there can't be that many competitors out there who could realistically support these lifetime requirements, and those that can will price accordingly. On top of that, your team has experience with this particular application and the customer's detailed requirements, giving you an advantage when it comes to bidding the project. Who knows, you could come out of a re-tender with a contract at a substantially higher sales price.
Best Answer
There are no guarantees, not even for the 68HC11. Ask your supplier what the policy on obsoleting parts is. Usually they send a notification with a last buy date. You'll have to buy sufficient parts to cover the remaining production years, or at least until you have a redesign ready. Depending on your relationship with your manufacturer (read: how many parts you purchase per year) you may get an early warning.
On one occasion, for a custom IC the manufacturer didn't discontinue the part, but raised the price to such ridiculous levels that we decided ourselves to stop production. This was an IC produced with an older process which didn't have much production anymore.
Like Olin says, look out for second sources. If your supplier discontinues a part you may still find it at other manufacturers. But scrutinize datasheets. Sometimes second sources aren't exact copies, and the details may need a engineering changes in your design. If you're lucky this is just a resistor value, if you're out of luck this could be an extra resistor.
Also, changing manufacturers may also imply a different price, and a (much) higher price for the part may be a reason for a redesign, especially if you're running large production.
edit
Mike mentions the Flash memory market as notorious for its volatile availability. This is probably due to continuous advances in the field, especially in memory size.
Also expect short life times for emerging technologies, like OLED. I've had OLED modules becoming obsolete before we finished our design!
Further reading
NXP sample product discontinuation notice