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68000

Obviously the  PowerBook 100. The Portable doesn't count.

68030

PowerBook 180  (not the 180c)
Less expensive than the 180c but sporting a larger (and still active matrix) 10" grayscale display. A full set of ports and better external video support than the 160. Doesn't use expensive 165c/180c RAM and lack of colour means batteries last a reasonable distance. A bargain at less than $US200.

68LC040

PowerBook 540
Tough one. They're all good. A toss-up between the  190, Duo 280 and 500 series. The 540 (grayscale) is unique in its ability to display 64 levels of gray on its active-matrix screen, has all the features of its more expensive sibling and is upgradeable to a 167MHz PPC. That 68LC040 is still fast enough with 20MB RAM or more. Twin batteries, ethernet, optional modem, optional PC card cage, all for less than $500 - and probably less than $450. I nearly chose the PB520 here as it has all the features of its more expensive siblings - except for the display.

603ev

PowerBook 3400/180
This is hard. Good arguments might also be made for the 1400 as it's G3 upgradeable. The 2400 is also a contender and also has that upgrade potential. But the 2400 was only available in the US and Japan. The 3400 gets the nod because it's a stacked, top-of-the-line machine with PCI architecture, fast processor, L2 cache, big screen, everything that opens and shuts. The 180 is the bargain of the bunch as it's nearly as fast as its 200 and 240MHz brothers but only around as expensive as the 1400/166. That makes it a Bargain.
 

G3

PowerBook G3/250
Another tough one. There are a lot of G3 configurations and apart from the cache-less G3/233 Series I, they're all great machines. The 250 from the first series is hugely fast with the 83MHz system bus (faster even than Series II or the current Lombard PBs which have 66MHz busses) and a 1MB backside cache which brings it almost to the level of the G3/292 or G3/300. Avoid the one with the 13.3" screen: get the one with the 14.1. Big and expensive but the G3/250 is the bargain of the piece.