As a former salesman of aftermarket vehicle security you're not 100% accurate. In essence Keyless entry or E&D makes gaining entry to the vehicle a little easier - on the basis that the car is always 'looking' for it's key(s). So a thief with the right equipment can scan your key in your house and 'relay' it to the car. Once the car is open they can then get access to the OBD port and program new keys.I am not really looking into the brands. Just the tech. The key has to send a signal to the car to unlock it and drive away. If there is a signal it can be intercepted and used.
On the figures I seen I remember Range Rovers were coming back often on the most stollen car brands (and that marked me because I did own a Range Rover, not with entry and drive though), but then Porsches, while not rare cars, are much much much less numerous on the road than most so it'd still make sense that comparatively very few of them get stollen, not enough to appear in stats, the tech still remain fundamentally the same though , signal > intercepted > stollen > curlling in a ball and crying .
With non-Keyless entry vehicles the code that is transmitted by the key changes every single time the remote control is pressed, and the codes are pseudo-random (they can't ever be truly random). So you can press the remote, record the code, and replay it - and it still would not open the car. I won't give more details on this, but wholly expect the vehicle's ECU is programmed not to accept data via the OBD port whilst an original programmed key is not in or near the ignition, hence why new remotes cannot be programmed in.
With regards to Keyless, a group of hackers advised a number of manufacturers that they had broken their security, and wanted a nominal sum to provide details on how, but the manufacturers would not accept this information, nor pay for it, and the rest as they say is history, sadly.
As for being able to program keys in using the OBD - sadly that's all part in fault of do-gooders in the EU, and them not understanding the relationship between consumer choice, and vehicle theft. Long story.