Help with simple OS upgrade and backup questions for a dumb old previous PC user...?

Question

Ok...have mercy on me, please...
I am not completely dumb, I know typical board etiquette, and I have searched for various answers (and found many)...but I just want to confirm my personal "research" and get all of this clear up before I proceed with this insanity.  I know I could probably search more, but this is taking hours, because of all my various questions, one leads to 10 more...
I have an iMac with Mac OS X Version 10.5.8 (which, though not mentioned anywhere?...is apparently "Leopard", right?  Told you I was dumb...)
Processor:  3.06 GHz Intel Core 2 Duo
Memory: 2 GB 800 MHz DDR2 SDRAM
My main goal:  install an app that was in the Mac App store.
However, with Leopard, I can't access the Mac App store with Leopard, apparently. 
I click on the Mac App store, and up pops up a Lion advertisement...telling me I should upgrade.  Ok, fine...probably a good idea, anyway...
But how do you upgrade to Lion?  Apparently through the Mac App store!
The web-redirects on the Apple site are amusing...taking me on an endless cycle...purchase Lion in the app store...click..."you need to upgrade to Lion"...OK...click..."you need Lion at the app store"...OK...click..."you need to upgrade to Lion to get to the app store"....etc.
OK...fine...google searches...ahh, I need to upgrade to Snow Leopard first, apparently!  Yes?
(Maybe the Apple redirects should detect that I have Leopard, and direct me to a screen that explains that I must upgrade to Snow Leopard...and then Lion!  Do you hear that, Apple?  Thanks.)
Anyway...so here's my plan:
1) Upgrade to Snow Leopard
2) Access the Mac app store
3) Upgrade to Lion
Question A:  With my iMac (specs above), is it really advisable for me to do this?  Can my computer really handle Lion?  It seems I barely meet the minimum with my intel core 2 Duo and 2 GB ram...yes?  Is this a dumb idea, even if "OK"?  I know that "minimum requirements" on a PC often meant:  "Well, it will work...but it will be slower than a snail and crash if you run 5 programs at the same time" (which I usually do...)  I don't want to upgrade if the "minimum" is really not enough. 
Question B:  If the answer to A is "not a good idea", then  do I just need a new computer (i.e. better processor)?  Or do I need more Ram?  And can I add Ram to this computer, and is it relatively easy?  I have added Ram to PCs tons of times, and you always have to determine type of Ram for your board, make sure they "match", or whatever, and then open up the machine and install.  Kind of a pain, but once I have the "right" type of Ram, opening the CPU and installing is within my abilities.  Will it be harder for a Mac?
= = =
Next:
When upgrading an OS on a Windows, you pretty much format the harddrive and start all over.  Back in the day I was a PC user, there wasn't really a "great" way to back up programs and files, so this was a nightmare.  You could NOT just back-up software.  You typically had to re-purchase and install it all from scratch.  Is this the same with Macs?  Furthermore, personal files were scattered all over the hard-drive for the individual software...so trying to back all that up to get it back on the new system = nightmare!  I hate PCs.
Anyway...so, my iMac has Time Machine.  I am pretty ignorant about this, and based on my previous PC backup program nightmares, I have a distrust for it...and don't really understand how it works.  But in any event, my external drive crashed a few months ago, and I haven't replaced it, yet.  So, I am replacing it soon and will get Time Machine back up and running...setting it up again, etc...leading to question C...
Question C: When upgrading from Leopard to Snow Leopard to Lion, what is the best way to ensure I keep all my programs and files.  My wife and I both access the computer, so two user accounts.  Does Time Machine really do a good job backing up everything and all things?  Is it just a matter of upgrade to Snow Leopard...then immediately to Lion...and then some sort of "Restore" from Time Machine?  Anything for me to "watch out for"...or to do when I buy a new external hard-drive and setup up Time Machine for the first time on it, in order to make this work well?  Will I have to re-install all the various applications I have installed on this thing?  (like with PCs?)
Thanks for any sincere help. 

Answer 1

yachadhoo wrote:
I have an iMac with Mac OS X Version 10.5.8 (which, though not mentioned anywhere?...is apparently "Leopard", right?  Told you I was dumb...)
Processor:  3.06 GHz Intel Core 2 Duo
Memory: 2 GB 800 MHz DDR2 SDRAM
Apple has discontinued support for 10.5, it's a plaque of our platform that Apple only supports the last two operating systems in circulation.
Where as on Windows you can run the same OS version for 10 years and get updates free (if not stolen), on a Mac we get one year, two tops now and if you don't upgrade and break all your third party software and hardware drivers in the process, then your denied security updates.
On top of that, the OS X upgrades tend to break your older hardware too, or slow it down so much that it drives you to want to buy newer hardware.
It's funny Apple places the AppStore on your OS X version along with iTunes and Safari updates, but then doens't supply necessary security updates, your machine may be compromised and here you enter vital credit card info, banking  etc. thinking you have a secure machine.
My advice, since that's a 10.5 era Mac, is to upgrade to 10.6.3 via this disk, then use Software Update until clear. You'll get security updates and your present installed 10.5 software will work in 10.6 using Rosetta.
http://store.apple.com/us/product/MC573Z/A
Rosetta is not avaialble in 10.7 so it could be a lot of your software will no longer function
http://roaringapps.com/apps:table
I don't see the sense in you buying all new software for a machine that's at it's end of life stage.
You can buy software in the AppStore with 10.6.
Question A:  With my iMac (specs above), is it really advisable for me to do this?  Can my computer really handle Lion?  It seems I barely meet the minimum with my intel core 2 Duo and 2 GB ram...yes?
You will need to buy 4GB of RAM to run Lion well, the 2GB is just a bare minimum, and your processor is a bit dated.
Lion 10.7 is certainly slower than Snow Leopard 10.6, in fact so many wanted to go back to Snow Leopard and one of the resons was Lion was slow.
So I wrote a User Tip, here, but the Tips were implemented only recently.
How to revert your Mac to Snow Leopard
Question B:  If the answer to A is "not a good idea", then  do I just need a new computer (i.e. better processor)?  Or do I need more Ram?  And can I add Ram to this computer, and is it relatively easy?  I have added Ram to PCs tons of times, and you always have to determine type of Ram for your board, make sure they "match", or whatever, and then open up the machine and install.  Kind of a pain, but once I have the "right" type of Ram, opening the CPU and installing is within my abilities.  Will it be harder for a Mac?
RAM is easy, you can buy it at Otherworld Computing or Crucial.com and install it yourself, there is a little door under the monitor.
Videos online at YouTube.
When upgrading an OS on a Windows, you pretty much format the harddrive and start all over.  Back in the day I was a PC user, there wasn't really a "great" way to back up programs and files, so this was a nightmare.  You could NOT just back-up software.  You typically had to re-purchase and install it all from scratch.  Is this the same with Macs?  Furthermore, personal files were scattered all over the hard-drive for the individual software...so trying to back all that up to get it back on the new system = nightmare!  I hate PCs.
Mac'soperaing system is seperate, it can be replaced or upgraded indepentantly of programs or user accounts on the machine.
There are some programs that install a kernel extension file at boot into OS X, those get knocked out, but those can be replaced with a new install of the software.
You should always backup your users files as those can't be repalced.
 Most commonly used backup methods explained
Question C: When upgrading from Leopard to Snow Leopard to Lion, what is the best way to ensure I keep all my programs and files.
OS X upgrades dont' affect User accounts but they can have a affect on programs installed, which most of your 10.5 programs likely will no longer work in 10.7
However they will (with a slight update) work in 10.6 just like before.
You need to backup regardless, I suggest a manual backup of users files to a storage drive, a 10.5 clone on another drive, the your ready to upgrade to 10.6
10.5 to 10.6 upgrade is rather painless, also 10.6 gives accelerated video drivers, so your machine will appear faster.
However once you install 10.7, you will slow down.
Does Time Machine really do a good job backing up everything and all things? 
No, you shouldn't rely upon TM, have a multiple backup stragedy, TM files are hard to access directly.
Is it just a matter of upgrade to Snow Leopard...then immediately to Lion...and then some sort of "Restore" from Time Machine?
No need to restore, OS X upgrades and leaves everything else in place, just some programs (with 10.6) or a lot (with 10.7) when you try to launch them they will fail.
Also when you connect TM it will do a substancial change to reflect the new boot drive.
If you were using TM as a "storage drive" thinking you can use the archived versions later, that wil change upon the new OS X  upgrade.
But in any event, my external drive crashed a few months ago, and I haven't replaced it, yet.  So, I am replacing it soon and will get Time Machine back up and running...setting it up again, etc...leading to question C..
You need not only TM drive, but a bootable clone and user files on a storage drive.
 Most commonly used backup methods explained
Will I have to re-install all the various applications I have installed on this thing?  (like with PCs?)
No, depending upon what OS X version you stop at depends how many programs no longer work.
You will have to buy a lot of new or upgrade versions with 10.7, not so with 10.6 only updates mostly because of Rosetta on 10.6 and not on 10.7
My opinion, since that machine is a bit dated, is to upgrade to 10.6, Software update to 10.6.8, and stay there.
Later on 10.8 is being released after this summer, you may want to consider getting a new machine with 10.8 a few months later to ensure all the bugs are worked out of it.
Your not a comptuer savvy person, you like most Apple users expect your machine to "just work" I think going to 10.7 will be a bad experience for you.
10.6.8 will server your needs until 10.8 is released and on new hardware where Apple will hold your hand for free for three months, 3 years with AppleCare.
Your not a "OS X upgrader type of a person" and Apple needs to get of thier collective assets and pay better attention to it's most common users.