Hello Ladderguy,
Great questions!
Yes, it is fine to skip the 2008 version all together and go straight from SA 2007 to SA 2009 - in fact, we recommend it!
The Simply Accounting database changed from 2007 to 2008. We went from the Access database to a MySQL database for stability and scalability reasons. This is particularly important to multi-user clients.
A few tips for installing:
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reboot all PCs before doing the install. It sounds obvious but if a Windows update was recently performed it will need a reboot (could affect .Net framework)
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during the install allow Simply to configure your Windows firewall. You will need to manually configure other firewalls if applicable.
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do the data-install on the server (this will give you a connection manager on the server.)
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convert the data locally and move the converted files (sai file and SAJ folder) to the server.
All of these tips and more can be found at www.simplyaccounting.com/install. You can also check out the install webinar for other useful tips. And just a recommendation, if possible move your installation date forward. Beat the rush and do it before tax time just in case you do need support
Oh - and yes, you can use Crystal Reports with SA 2009.