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Why would you want to limit yourself to one link? Get a respectable number primarily for the value of driving pre-qualified traffic to your site and secondarily for PR.
I suspect that if you truely got 1000 with PR of 5 you would certainly get some favorable impace in PR. But better than that is 1000 Web sites sending you traffic and allowing you to present yourself favorably for making a sale.
1000 links is alot and alot can change in 2 months, 6 months, a year and so on.
Forward thinking means believing today's decisions are in the distant past, so...
My question is... what is the likelihood that the single link from a PR8 page:
Will sustain you in the far distant future, where many things can happen, new strategies, domain change, out-of-business, and about 1,000 other negative potentials
On the plus side... a single PR10.
or...
1000 potentials that could have the same negative or positive effects.
Diversification means that you have a strategy and contingency plan, a one hit wonder isn't a strategy and doesn't offer any contingencies.
It will hurt alot if losing 1 from the first and you will not even notice if losing 1 from the other.
Also just having 1 PR8 or PR9 link could be viewed suspiciously. Or having 100s or 1000s of links from only one site. These are perhaps not part of the algo yet but who knows that the algo will not be refined to take these factors into consideration in a month or two!
Anything that is "unnatural" can only work for two or three months IMHO!
The nearest we'll get is that it most likely takes _many_ pages with low PR to outweigh one with high PR. As others have pointed out this means that gaining an incoming link with high PR is a big win and losing it is a big loss.
As I see it one should diversify the tactics in terms of gaining incoming links with PR. Have a few with high PR if possible _and_ a lot with lower PR.
And once again: What's really important is that your incoming links are relevant and bring motivated visitors.
Yes, I know that you know!:-)