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I have done this on my 6' round table successfully.
My biggest suggestion would be to work from the middle outward.
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Where is the middle of a round table? JJ
With a more serious reply...
I have made a table with a one-piece padded rail. It looks really good with no creases on the top (they are all hidden underneath). I got some tips from the various sites at
www.homepokertourney.com (specifically the Junell table).
Basically, you lay your rail on top of the piece of vinyl and cut trangles at the ends. It's easier to see with pictures (see Junell's instructions at HomePokerTourney).
I actually started at the end of the table and worked towards the middle, pulling the vinyl towards the middle.