What is the best sequence of upgrading: SSD, OSX Mavericks, iPhoto Library?

Question

Working on breathing new life into / upgrading my wife's mid-2009 MacBook Pro (Macbook Pro 5,5 - Core 2 Duo, 2.26 GHz, 13"). Currently running OSX 10.6.8 Snow Leopard.
So far: I have upgraded the RAM to 8 GB from 2 GB, and replaced the battery which recently reached the end of its life.
Next up: SSD upgrade and possibly OSX upgrade to Mavericks.
My questions:
(a) What is my best upgrade path (order/sequence), given the few things I want to with this machine still?
(b) Are my plans and reasoning below sound?
1.Upgrade the 120 GB hard disk to a 240 GB SSD. I have a SanDisk Extreme II 240 GB (although I know this MBP won't fully utilize the SATA III, I got a good deal on it and plan to use it as an add-on drive somewhere when/if this MBP logic board fails eventually), and a USB to SATA adapter for prep work.
Plan: Attach the SSD via USB adaptor, initialize and partition with Disk Utility (Journaled, GUID Partition Map so it's bootable), clone existing hard disk using Super Duper or CCC (recommendations welcome--I'm on a budget ). Set TRIM enabler, and other recommendations per Upgrading Your MacBook Pro with a Solid State Drive
Reasoning: Doing this SSD upgrade first will give me more free space for updates/changes I plan under #2 and #3 below. (For example, current drive has 11 GB free, which is not much room to try and upgrade to Mavericks now before swapping out for SSD.) Additionally, Mavericks will perform much better on the SSD, per other threads I've read with similar MBPs.
2. Upgrade OSX 10.6.8 Snow Leopard to Mavericks.
This is where some of my Mac knowledge is lacking: Is it best to upgrade here (what I've read so far indicates it's pretty seamless), or to install Mavericks freshly on the SSD and then use Migration Assistant to import from the old hard disk? I hesitate to do the latter, since this Mac still has some messes from a previous migration (see #3).
Coming from a Windows background, I have my biases, but I don't know if the jury's still out on performance differences between fresh Mavericks installs versus upgrades--any light to be shed here?
3. Fix iPhoto '09 Library and Consider Upgrading to iPhoto '11. Through reading on the great forums here I have concluded that my wife's photo collection currently exists in a weird place - 68 GB under /Previous Systems/<date of MBP upgrade from Macbook>/Users/<username>/Pictures/iPhoto Library. This seems to be left over from when she copied her iPhoto Library from her old Macbook, before this MBP. (Before I sat down to write this post, I had noticed there was an iPhoto Library (much smaller size, just a few GBs) in the normal place, under /Users/<username>/Pictures/iPhoto Library/ -- but now I don't see it, so maybe I goofed up and either lost that or imported it into the above library. Either way, that was going to be one of my questions!)
Should I move this "Previous Systems" iPhoto Library to a more normal place?
If I do again find extraneous photos or libraries outside of it, how best should I bring them back into one -- or a better question might be, how do I ensure THIS becomes the primary iPhoto Library going forward? (links to threads also appreciated -- I have come up short)
If this machine is now on Mavericks, is it a best practice to also purchase iPhoto '11? Eventually, our next Mac will come with it so it may be worthwhile eventually upgrading (I don't know if it is urgent, though).
Overall, does this process make sense? Any glaring gaps? Thank you for your time and wisdom!
Ryan

Answer 1

Thanks Melophage. I've been looking into my options, together with the advice you gave. It seems like I can salvage quite a bit of data after a fresh install if I follow the steps here - OS X: Manually migrating data from another Mac. However, applications are my (only) concern -- for my iLife suite apps (which as I mentioned, are old -- '09 editions) how can I restore those after installing Mavericks fresh? Can I just plug in the original Snow Leopard disc that says applications on it, to install? Or would they show up in Mac App Store (I think not since they are so old and I haven't purchased '11 with this account yet).
My wife's computer also has some third party apps which would be a pain to reinstall but not end of the world, I suppose. Another route of migrating and keeping these (but still doing a fresh OS install) might possibly be according to OS X: How to migrate data from another Mac using Mavericks, which is really designed for multiple computer copying. But with the SSD external, could I install Mavericks and then take a Time Machine backup of my internal (original) HDD, including those apps, and then follow these steps to import them into the Mavericks install on the SSD, once I booted into it? Does that make sense?
After some further reading on the subject, I found a lot of difference of opinion (especially on some MacRumor threads) about whether to install fresh OS X or upgrade, but I guess if the install ends up cleaner it could be worth it to install a fresh copy.
Any comments on the above approaches, or thoughts from others here? Thanks again for your help.