I have a Crazy Taxi upright and i've swapped in loads of things.
Here's what i tried, in general pretty much everything works, sometimes some minor adjustments needed (i didn't dig into which hardware you need to play the games, you should first look what you'd like to play ^^, the rest is easy):
- Initial D 1-2-3: Straight swap (assuming you have the hardware ofc) and playable out of the box. Note that the shifter will not work so you will have to drive on automatic. The DOWN shift will change views on default Crazy Taxi wiring, and UP shift will do nothing). Rewiring the shifter to work if you'd like is very easy, but then you will need at least an extra button somewhere to change views.
An Extra note i'd like to add, since Crazy Taxi has no cardreader, and Initial D really needs a card reader, though this game is very playable, it's no fun at all without cardreader. You can't get into the tuning shop to upgrade your car, and you can't save your progress, so you will just drive a stock car forever without any tuning. This game's all about tuning and saving progress to get better times etc, so it kinda makes it a dull game while it's really not.
You can add an ID Cardreader to your cabinet (it really has to be the ID cardreader, not other sega cardreaders_) but they are expensive. Very expensive ^^
- Outrun 2 (Normal or SP): Straight swap (assuming you have the hardware) and playable out of the box. Same as Initial D, shifter will not work out of the box, DOWN shift will change views, UP shift will do nothing. Also here, you could rewire the shifter if you please.
- King of route 66, straight swap. DOWN shift will change views defautly
- Jambo! Safari, straight swap. Your DOWN shift will defautlty throw the lasso.
On regard of F355 Challenge, i'm pretty sure this also works. The DX version of the cartridge uses 4 Naomi motherboards (custom ones), 3 for the 3 screens, and 1 to control and link all the boards. Do not get the deluxe cartridge, it will boot and work but it will run very very slow and be unplayable.
The normal cartridge however will work, i'm just pretty sure this is not a game you want to play in an upright, i just think you will completely miss the experience of F355 and it won't be fun. And i'm sure the shifter will not work defaultly.
All in all, i got my Crazy Taxi cabinet exactly for this, to easily swap in some games from time to time, without needing to much space. And i didn't mind that in most other games the shifter didn't work (i didn't want to rewire).
Though now i have lots of 'real' driving cabs, the Crazy Taxi upright is still a nice cabinet for quick swaps
I personally can really recommend Outrun 2, it's a great game and very well worth spending some money on.
If you need any more info or tips, let me know, i swapped in lots of stuff lately.