I grew up water skiing, tubing, slalom, knee boarding, wake boarding, bare footing, skurfing, and have even ridden a piece of ply wood with wax on it behind a boat, among other things. Now that my credentials are out of the way on to the question.
The bridle that BassDocktor linked you too is going to be your easiest set up. It is very strong and has few safety concerns.
Next, you are right to be concerned that a pole will rip out of you bass chair pedestal. It will. It would need reinforcing at the top of the pole to eliminate the torque created at the base. Take a look at this design.
http://www.basspro.com/webapp/wcs/stores/servlet/ProductDisplay?storeId=10151&catalogId=10001&langId=-1&partNumber=32844&hvarTarget=search&cmCat=SearchResults
As this one is designed you will only need to reinforce the base plate of your bass seat to prevent it from lifting up. This is much easier than trying to prevent torque.
Now on to the benefits of the pole. Being that your rope it attached to something in the boat you can connect, disconnect, retie much quicker and easier. The elevated position of the rope is easier for skiing. The few degrees of up angle actually help pull the skier up out of the water. This became very apparent when I built an 11 ft pole for wakeboarding. I could jump much higher.
If you are only occasionally going to pull behind the boat and just tubing I would get the bridle. If you are going to get into slalom and wakeboard for 4 hours a week I might consider the pole.
Ps tubing is the most stress I have ever seen put on a boat. It is substantially heavier than a pair of skiers. I have seen two ropes break in 10 years from tubing and zero from anything else. Boats always take longer to get on plane with tubers than any other tow behinds. Check the instructions on that or any other pole to see that it was designed for tubing.