Replacing a desktop in an SBS 2011 domain: Am I doing something wrong?

I guess I haven't setup replacement desktops for a while and am either rusty or doing things wrong.

How long does it take for you to setup a replacement computer for a user on an SBS domain?  And would that answer matter for a workgroup? or non-SBS domain?

I am not talking about the unboxing the machine, setting it on the desk, re-snake cables, replace the mouse and keyboard and those things.  I am thinking more about the software and configuration of the machine.

Beyond running http://connect which will give them share mapping , printers et al, I then do a long list of manual tasks. These are typically for the small businesses I deal with that have 5 to 10 users so are there automation processes that are justifiable for small domains like these where this situation is very infrequent?

I'm thinking of tasks such as:

Being smaller businesses with infrequent computer replacement, we buy Office as OEM. That requires manually running the initial install and entering the license key to activate. But no need to make a Microsoft account, if there's a bright part to this.

Installing quickbooks from a copy of the install disk stored on the server then manually entering the license key, installing updates to get to the latest R version, then activating the installation

Installing LOB apps such as Asset Keeper, ecopy, source capture check scanning software and others either from copies of the install disk on the server or the install CDs themselves

While opening Outlook for the first time and walking through the account setup to the exchange account is so enjoyable in this process, compared to other steps here and previous POP accounts, things like their signature, NK2 list, check spelling before sending and other nuances I am setting manually.

Installing Shadowprotect, manually entering the license and activating then setting a continuous backup including the backup path, hours and frequency for the backups, encryption key, setting the app's agent settings including where to send reports, frequency to send reports, title of the reports and similar nuances.

From the old computer checking for files and setting that are on the machine and copying them over, such as the QBW.INI file that shows their list of recently accessed quickbooks databases, wallpaper image and setting the desktop wallpaper, favorites in IE and bookmarks for chrome, NK2 files et al.

Also fonts: inevitably, some users have collected fonts in windows\fonts that didn't come with the computer and will notice they are not on the new machine.

At the same time, being older machines I don't want to simply dump all of the c:\users\%username%\appdata files and bring over clutter from apps that are no longer being used.

Or am I setting expectations from users that their new machine will look very much like their old machine.  That is my goal. Am I wrong to lead them to expect that?

Am I wrong to admit that I have never used Windows Easy transfer? I envision it would bring in too much not needed clutter and not bring over everything desired so a mix of automation and manual migration would cause more issues and delay things further?  Manually looking at the  old machine and seeing something that should be moved to the new machine, rather than move it, I need to wonder if Easy transfer already moved it and if not, then manually moved it?

As much as a nice new machine is so much more enjoyable for a user and for me to manage, the migration has become such a chore for most clients.

I would very much like to hear the thoughts from people here who are more experienced than myself.

Thank you.
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Cris HannaSr IT Support EngineerCommented:
Until you decide to get away from OEM installs and go with VL and creating disc images, no there really isn't an easier way.   And I suspect that replacements are rare as you indicate, which makes it even tougher

Documentation will be your best friend, so you don't have to figure out again what you did the last time at that particular business
BeGentleWithMe-INeedHelpAuthor Commented:
Thanks Cris, but being small businesses, each machine is a bit different on what they need.  But a disk image would involve building a machine - win 7, load all the apps, then take a snapshot?  when an new machine comes in, put the image on the machine, THEN run http://connect (not that it's that important here, just wondering)?  

How would taking settings / files that have collected on the machine over time be handled though? Things like favorites, outlook signature, wallpaper, etc?  imaging wouldn't help with that, right?
Cris HannaSr IT Support EngineerCommented:
You would want to create updated images from time to time to keep up with those changes
As for profiles, many great tools out there.
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BeGentleWithMe-INeedHelpAuthor Commented:
we're backing up the machines using shadowprotect.  But to pick out the needed files and registry settings for apps being used currently vs. apps that had been installed / removed some time ago, but their uninstall apps, leave things in the registry / files and folders in the app data folder, etc.  Seems to need to be a manual process?
Windows Easy Transfer is your answer. You have a lot of questions and concerns but you said you have never used WET. Use it. That's what it is for. Other than this, there is no other automated option to accomplish the same task that I am aware of. You may also want to look into roaming profiles. Use your server to hold the profile settings and it will not matter which machine the user logs into.
Cris HannaSr IT Support EngineerCommented:
WET is really a consumer or end user tool.
USMT (User State Migration Tool). Is an ITpro tool.

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BeGentleWithMe-INeedHelpAuthor Commented:
Thanks guys! In the yahoo SBS forums people have poo poo'd roaming profiles over the years - slows things down?
Cris HannaSr IT Support EngineerCommented:
Roaming profiles can be bandwidth hogs and significantly slow start up times depending on where employees store their files
Roaming profiles will not cause bandwidth issues on 5-10 user networks. And going VL is not practical for such small networks.
Cris HannaSr IT Support EngineerCommented:
If you 5 users each with a couple hundred megs of My Docs that has to synch every logon or log're going to see temporary bandwidth issues
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