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Exchange 2010 - to split or not to split

Hello, I have a fairly large customer whos users do not delete the trash folder in their Outlook.  Consequently, their Exchange datastore grows by leaps and bounds.  With this growth, they continue to run out of room on their virtual disk that is setup on a SAN.  We need to constantly increase the size of the disk to accommodate.  This is a fine solution short term but we will not be able to sustain this growth.  

Currently, the company houses a Vmware Esxi environment with two hosts attached to a SAN.  The Exchange store database is currently at 477GB.  The virtual disk that this resides on currently is a total of 730GB.  The SAN has only 230GB of space left.

Questions:  
1.  How big should we allow the Exchange store to get?  What is recommended with 2010?  Exchange has locked up twice in the past two weeks and I'm not sure if it could be related to the size of the database.

2.  I'd like to ideally push my client to Office 365 as I feel that it would be a great solution for them.  Unfortunately, the internal IT user wants me to split the database up so that the higher up management team's emails reside on one Store and all other users reside on another.  This solution will allow us to be able to restore quicker in the event of a failure but does not address the space issue.  Is splitting the stores up recommended?  What are the pro's and con's to doing this?

Again, Office 365 is what I would like to see them get to but the internal IT person is "old school" and is hesitant to put anything to a "cloud" solution.  The things that I want to avoid are:

1.  Supportability.  I dont' want the splitting of the exchange stores to cause a "cluster ****" on the environment so that my team and I spend endless amounts of time supporting.  Easy solution is better for us as it is more manageable
2.  I dont want the time invested to split the databases up and migrate email to that to overshadow what an Office 365 migration would cost the company.  In the end, if we do go the route of splitting the scopes the company is STILL on Exchange 2010 which is now 4+ years old.  I would like to point them to 365 as they will be on an updated platform.  I would hate to think that the money cost to them for splitting the scopes would be higher then 365 and in the end they are still on old technology.

The company currently houses approximately 100 employees - which is a large company for us.  We are a VAR and outsourced IT company for local businesses.

Thank you for your recommendations and if you have questions for me...by all means ask away!
Cheers!
Mike
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Adam Farage
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It makes perfect sense Adam!  Thank you for your input.

Cheers
Mike
Noo problem. Enjoy the new years!