Hi Paul
2008 iMac, that’s some good milage, basically 10 years. Good call to go with 
SSD storage when you get a new machine, I will however recommend you look at at 
least 512 GB to be a bit more future proof.
I presume you have a iCloud account with all your contacts, calandar etc synced 
to the cloud, in that case this part won’t be a issue at all when moving to a 
new machine.

The easy option will be simply to restore your new machine from your current 
Time machine backup, this will basically restore everything for you, apart from 
maybe entering some usernames and passwords you will be up and running in no 
time with a machine layout you are familiar with. This process is totally 
accessible using Voiceover.

The second option which will take a lot more time and effort is starting with a 
clean machine and manually reinstalling everything, after a couple of years of 
use and collecting junk this is not a bad option. I personally do it on my 
machines every 3 years or so just to get rid of old unused stuff.
With this option everything in your iCloud will still download seamlessly on to 
the machine and will only take a username and password.
The fun comes in with restoring all your apps, you’ll have to go download these 
manually from the appstore again or look for them on the internet. You’ll have 
to remember usernames, passwords, licence codes etc. a nice trick when doing 
this is screenshots for sited people, if you can’t see screenshots then you’ll 
have to manually write everything down in notes or somewheree. Then again if 
you still have your old machine up and running next to the new one, you can 
just go back and forth for example threw your applications folder to see what 
app you have to install next.

Good luck with this
 
> On 31 Jan 2018, at 19:23, dan d. <dandun...@gmail.com> wrote:
> 
> 
> Wih the backups in place wait until the current machine breaks.
> 
> For the vast majority of whatt people do that machine is fine, which can also 
> be said for an osx older then that one.
> 
> The constant urge to have the latest beyond what one needs has always been in 
> my mind  somewhat irrational.
> 
> On Tue, 30 Jan 2018, Paul Hopewell wrote:
> 
>> Hello,
>> I am currently using the latest El Capitan 10.11.6 on a late 2008 iMac which 
>> alas will not support any more recent Mac OS releases.
>> It is becoming apparent that some time soon I will have to replace this aged 
>> iMac with a new one, probably the model with a 20 inch display and a 255 GB 
>> solid state disk drive. On my current iMac I run time machine to an external 
>> hard disk drive and also du periodic SuperDuper backups to the external disk 
>> drive and also to a USB memory stick..
>> I am put off from replacing my aged iMac by the thought of migrating all my 
>> data and applications. In addition to the obvious user files I have a lot of 
>> contacts, an extensive calendar, lots of iBooks and iTunes files, Safari 
>> bookmarks, passwords and secure notes in 1 password, Infovox voices, VMware 
>> fusion and a Windows 7 virtual machine, and difficult to remember 
>> preferences for some of my Apps. Rather than migrate everything it would be 
>> a good opportunity to get rid of now unwanted Apps and to start as many Apps 
>> as possible with a clean slate.
>> So how should I best do this migration in a VoiceOver friendly way?
>> Best regards...
>> 
>> Paul Hopewell
>> 
>> 
> 
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