My '08 also has a cup holder, and I've never had clearance issues with OBD2 port. I've used like 4 different ones over the years.
I've used 3 cheapo china ones on and off in various sizes (because I keep giving it away to friends and/or misplaced them), and now I'm using OBDLink MX, which looks to have similar footprint as Kiwi.
The only difference, in my experience, between the sub $20 chinese OBD2 reader vs $70+ ones is that the expensive ones had much higher data rate due to different IC being used. However, the cheapo ones sent out enough data points, and I was only logging at 10Hz, so there was no advantage to be had going with a nicer one.
For apple, you need to use the wifi version. They don't let you use the BT version.
I've used RaceChrono for years to my satisfaction, but iphone folks seem to use Harry's Lap Timer a lot.