Questions about OS upgrades

I currently have an 2.4 GHz Intel Core 2 Duo desktop running OS Snow Leopard (10.6.8).
I'm happy with it, although when I wanted to download an Adobe Illustrator free trial today, it said I needed at least 10.7.
I'm just wondering about the philosophy behind doing system upgrades.   I'm sure many people automatically upgrade as soon as an update is available.  But some people like me keep what they've got until they absolutely need to upgrade.
In my case, everything runs fine with one exception I mentioned.   So here are my questions:
1. If I did want to upgrade to OS 7, how would I do that and how much would it cost?  
2. Would I need to worry about losing anything in the process? 
3. And if I were to upgrade, why not just go all the way up to Mavericks (10.9)? 
4. Might there come a time that I will absolutely need to upgrade?
Thanks for your considered and wise answers!

James Snedeker wrote:
So here are my questions:
1. If I did want to upgrade to OS 7, how would I do that and how much would it cost? 
Call the Apple Store and ask them.  You will be given a download code after purchase.
2. Would I need to worry about losing anything in the process?
You should have a backup.  No worries.
3. And if I were to upgrade, why not just go all the way up to Mavericks (10.9)? 
Because you first must determine if you meet ALL of Mavericks system requirements.  Also, the decision is up to you if you want to upgrade further or not.
4. Might there come a time that I will absolutely need to upgrade?
Yes.  Depends on the software and/or hardware you are using.
Thanks for your considered and wise answers!
See Kappy's instructions on how to upgrade to Lion in the following thread:  https://discussions.apple.com/message/24634710#24634710 

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