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Moving On From Whsv1 - Advice?

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[I know this is similar to a lot of threads on here, but I couldn't find an exact match - feel free to point me at one]
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Loved WHS, (a product from Microsoft that just works!?) - it's been reliably ticking away for years on the original HP MediaSmart ex470 box that I imported from the US because they never bothered to sell them here in Australia.

But, I'm kind of disillusioned with Microsoft for pretty much dropping the product line, and as a company they seem to becoming less and less relevant... so time to move on, before my EX470 grinds to a halt or explodes...

Currently using WHS for:
1) NAS style storage: Documents and Media etc
2) Full computer backsups via WHS Extender
3) DNLA server
3) Sharing 2x printers
4) Remote access to files and PCs
5) Home webserver

I would appreciate thoughts on replacing this functionality with something more modern. I'm thinking:

#1 & #3 - a Dropo 5N.

Pros: An extra drive bay (running low on space so extra room would be nice); more modern hardware; SSD caching accelerator.

Cons: Expensive - $600 with no drives; no eSATA or USB3.0 ports, so no chance of adding any more storage externally.

Unknowns: Given how full my drives are, I'm not sure how I would go migrating across without buying another set of drives, but I can probably do this piecemeal. Not sure how power efficient this is compared to the EX470. Unsure how well the box acts as a DNLA server. There doesn't seem to be an option to back part or all of the Drobo up to an external disk drive. I currently do this for my photos etc and take it off-site, in case of fire or burglary etc.

For #2, I believe I can purchase backup licences from Drobo to do automated backups of my PCs. Has anyone had any experience of this? Is it rebranded Acronis software? Any other third party software recommended? I would like it to be as seamless as WHS is - boot off a USB key to restore, online access to files etc.

For #3 I'm thinking of getting new printers that have wireless or wired LAN ports, or maybe a print share box for my existing ones. Does anyone know how well these work? Is there any solution that gives shared access to a scanner?

#4 and #5 - I'm not sure on this, but I suspect I can get a cheap stand alone box or some router with fancy firmware. The web hosting isn't essential, but (secure) remote access could be nice.

Any suggestions welcome!

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