Upgrade the old iMac before migrating to a new one or not?

Hi all,
I am planning to buy a new iMac and would like to migrate some of my stuff to it from an old iMac. And then I would also like to migrate some of my stuff from a still older MacBook onto this old iMac. Complicated enough? :-)
In short:
Step one: stuff from my 5 year old iMac with OS 10.7.5 Lion on it migrates to -----> a brand new iMac with Yosemite.
Step two: stuff from my 8 year old MacBook with OS 10.5.8 on it (and not upgradable any further) migrates to -----> the 5 year old iMac with OS 10.7.5 Lion on it.
Now, my questions are these:
1) Should I first upgrade the 5 year old iMac with OS 10.7.5 Lion on it to Yosemite before migrating my stuff from it to a brand new iMac with preinstalled Yosemite or not? Recommended, not recommended, neutral, what?
2) If the answer to the 1st question is "yes" (recommended), will I then be able to migrate my stuff from the 8 year old MacBook with OS 10.5.8 onto it? That is, will the two migration assistants (of OS 10.9 and OS 10.5) "talk" to each other at all?
Any further tips will be hugely appreciated!
Lots of thanks in advance!

Hi rkaufmann87,
thank you so much for your reply!
I am afraid you misunderstood me a little bit… While you kindly explain to me ways of how to migrate my data from one computer to another, my question was not so much about "how" but rather about "whether":
a) should I first upgrade my old iMac (with 10.7.5 Lion on it) to Yosemite before migrating its data to the new iMac with preinstalled Yosemite? Will it help in any way or is it irrelevant?
b) and if the answer is "yes" (i. e. upgrade the old iMac to Yosemite), whether the migration assistant on the 8 year old MB will then be able to "talk" to its counterpart on the now upgraded old iMac?
Perhaps this too might help:
What I am trying to do is make two computers out of three -
1) My wife's 8 year old MacBook will most probably go to the dustbin. Before it does, I would like to migrate her data to my 5 year old iMac which will then replace her MB (in the dustbin) and be hers forever after.
2) I will certainly have to migrate my own data from my 5 year old iMac to the new iMac which I am about to buy.
So the question remains: upgrade the old iMac for both purposes (s. above - #1 and #2) from Lion to Yosemite - yes, no, doesn't matter, what?
Many thanks again!

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