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Thanks for the thoughtful questions. You have given a lot of thought to how you might map your skills into SAP. Let me go through each of your questions:
1. I don't necessarily think it's easy for a DBA to break into Basis, but I agree with you that this is the most natural entry point into SAP from your current skills. Remember that some Basis roles are much more DBA-focused than others. Most Basis folks I know these days generally work with a DBA who specializes in that area, but it's still valuable to have DBA know-how if you're a Basis person and that is the most logical entry point into SAP for a DBA.
2. Yes, I think Basis is the best place for you to try to enter the SAP world. I think the functional role would be too much of a leap for you at this point. But, once you break into SAP, you could then look to move into a functional role down the line.
3. I don't think Basis will be around much five years from now as a core skill, but the natural evolution of the Basis administrator, the NetWeaver administrator, should be alive and well. It's not the easiest area of SAP to succeed in, but companies certainly need these kinds of folks and will continue to. The only risk you run is that if more and more companies go the way of hosted applications, then on-site system administrators won't be under the same level of demand. But while I do expected hosted applications to be more of a factor five years from now, I don't think it will take away from the need for on-site system admins.
4. No, Basis isn't the most financially rewarding area of SAP, there are many niche functional areas that pay better, but Basis can be one of the highest paying contract roles on the technical side of SAP, with the possible exception of BW, XI, and Portals - and keep in mind that good Basis people can touch on those three areas also.
5. Sure, if you can afford to take courses, go for it. If you go through my SearchSAP archives, you'll see that I am pretty skeptical of the power of certification when it comes to landing your first SAP job. But it's still valuable knowledge. I would recommend you use your course and training budget to learn forward-thinking technologies. So instead of taking a Basis admin course, take some kind of NetWeaver-related course instead. The biggest challenge you need to address right now is to spend more time learning where SAP is going. Basis is rapidly becoming yesterday's technology, so be careful, it's harder to catch a train from behind.
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