EXPERT RESPONSE
I would certainly recommend implementing now and upgrading later for a few different reasons.
First, the current release of the Oracle E-Business Suite (11.5.9) is quite robust and has recently introduced a number of very valuable features. It is being used by many organizations but it has not been out a terribly long time. Therefore, by the time you implement you are going to be working on a widely used version that is not about to go obsolete.
Second, I would caution waiting and becoming an early adopter on the next release unless there is a critical feature that you cannot implement without. It is easier for organizations that have a wealth of experience with the technology to be more leading edge than it is for new organizations.
Finally, the latest release has many value-added features that will likely benefit your organization. Assuming this is the case, you will gain by implementing sooner rather than later.
On the second question, the answer is quite long. I think the best answer is to get assistance from an organization who has successfully implemented the Oracle E-Business Suite many times before. This organization should have both the necessary functional and technical expertise and be experienced with organizations similar to your own.
If you know of such organizations that is great. If not, please feel free to contact me directly for a list of such organizations.
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