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I am sure you will hear from advocates of both models. Also, some of your criteria will lead to different conclusions. For example, the 96 is easier to work on (IMO), but parts availability is probably (?) better with the 99, since it is a later model.
As a long-time SAAB owner (36 years), if I had to choose, I would probably choose the 96, with the V-4 engine. The 96 is a simple car to work on, whether it's mechanical items or body parts (the fenders bolt on, the 99's fenders are welded on). I have owned both 2-strokes and V-4s, and I would choose the V-4 primarily because it gives the car enough power to be really fun to drive. I think that most people would find a 96 with a 2-stroke to be pretty underpowered by today's standards. Although the 2-stroke engine is much simpler than the V-4 (no valves and associated valve-train components), and therefore should be more trouble-free, I think that parts could be a real bear to find, since the engine has been out of production since 1968. The V-4 engine was a Ford engine, and a version of it was used for stationary industrial applications even after SAAB stopped using it, so parts should be relatively easy to find. Also, all V-4 engined 96s had the four-speed transmission, while with the 2-stroke you run the chance of getting one with a 3-speed transmission, which, with only 40+ horsepower with the 2-stroke, makes performance truly underwhelming! Finally, the V-4 can be personally modified for even greater performance than it has stock - there are several web site with information about "hotting-up" the V-4 engine. The 96 ia a basic car - don't expect many niceties or sophistocated features.
The 99 is a more sophisticated design than the 96. It has more creature comforts, and insulates you more from the roughness of the road and the noise of its mechanicals. It is probably a better car for longer trips - you will arrive more rested than in a 96. However, the very things about it that insulate you from road noise, roughness, and stress also make it less fun to drive than a 96, IMO. Also, it is more mechanically complex than the 96, and will probably take more time and cost more to repair. If you decide on a 99, get one with the SAAB manufactured engine - stay away from the early years of the model (1969 through 1972, I think) with the British engine - those engines are trouble! Also, prior to 1975, when SAAB came out with what SAAB mechanics called the "King Kong" transmission, the 99's transmission was weak - lots of them needed rebuilds prior to 100,000 miles, including the one in my '71 99, which died at about 65,000 miles. So, your best bet in a 99 is probably a 1975 or later model.
SAAB installed its first turbocharger in the 99 in, I think, 1978. Should you buy a 99 turbo? I would be very wary. First of all, these were the first SAAB turbos, and many of the design features that ensured long-term reliability of SAAB's turbos were not included on these first models. Second, the people who bought these first 99 turbos tended to drive them hard, even very hard, so they may be beat. I understand they are a lot of fun to drive, but unless you can be sure that it has had by the book maintenance, I would tend to stay away from a 99 turbo.
Pricing? I have noticed that prices on good condition 96s have started to edge up, presumably because of their rarity. The V-4s seem to bring higher prices than the 2-strokes. Check the classifieds on SAABnet - prices for good condition, late model (1968-1973) 96s seem to vary from $1500 to $4000. The 99 seems to be SAAB's forgotten model, and you can probably get a good condition, non-turbo 99 for less money than a similar condition 96. Most of the prices I have seen are in the $1000 to $3500 range.
Hope this has been of some help, and good luck whichever model you decide to go with!
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