Updating to new operating system from circa 2008 OSX

My 2008 MacBook Pro is running Mac OSX 10.5.8. Recently I tried to use a Mac application I had downloaded but was told that it wouldn't work because my OS is so outdated (I haven't changed the OS since I got the Mac).
I went to an Apple download site to try to download a more recent OS like Mounatin Lion, but this wasn't possible because my machine needed a more recent OS just to be able to download a new OS properly (!!). Kind of a Catch-22!
I inquired with a tech person by phone who said I would have to buy an older (but not as old as OSX) operating system on something portable, like a USB zip drive. Then when that was loaded up, my OS would be able to understand the Apple download site enough to download the most recent OS versions, like Leopard or Lion or Mountain Lion. Is that really necessary?
Can this be solved by just taking the laptop to an Apple Store for an OS upgrade? I really don't want to have to leave the machine somewhere for a period of days, baby that I am. But I will if I have to.
Thanks very much for any help.
Will

Upgrade Paths to Snow Leopard, Lion, and/or Mountain Lion
You can upgrade to Mountain Lion from Lion or directly from Snow Leopard. Mountain Lion can be downloaded from the Mac App Store for $19.99. To access the App Store you must have Snow Leopard 10.6.6 or later installed.
Upgrading to Snow Leopard
You must purchase Snow Leopard through the Apple Store: Mac OS X 10.6 Snow Leopard - Apple Store (U.S.). The price is $19.99 plus tax. You will be sent physical media by mail after placing your order.
After you install Snow Leopard you will have to download and install the Mac OS X 10.6.8 Update Combo v1.1 to update Snow Leopard to 10.6.8 and give you access to the App Store. Access to the App Store enables you to download Mountain Lion if your computer meets the requirements.
     Snow Leopard General Requirements
       1. Mac computer with an Intel processor
       2. 1GB of memory
       3. 5GB of available disk space
       4. DVD drive for installation
       5. Some features require a compatible Internet service provider;
           fees may apply.
       6. Some features require Apple’s MobileMe service; fees and
           terms apply.
Upgrading to Lion
If your computer does not meet the requirements to install Mountain Lion, it may still meet the requirements to install Lion.
You can purchase Lion by contacting Customer Service: Contacting Apple for support and service - this includes international calling numbers. The cost is $19.99 (as it was before) plus tax. It's a download. You will get an email containing a redemption code that you then use at the Mac App Store to download Lion. Save a copy of that installer to your Downloads folder because the installer deletes itself at the end of the installation.
     Lion System Requirements
       1. Mac computer with an Intel Core 2 Duo, Core i3, Core i5, Core i7,
           or Xeon processor
       2. 2GB of memory
       3. OS X v10.6.6 or later (v10.6.8 recommended)
       4. 7GB of available space
       5. Some features require an Apple ID; terms apply.
Upgrading to Mountain Lion
To upgrade to Mountain Lion you must have Snow Leopard 10.6.8 or Lion installed. Purchase and download Mountain Lion from the App Store. Sign in using your Apple ID. Mountain Lion is $19.99 plus tax. The file is quite large, over 4 GBs, so allow some time to download. It would be preferable to use Ethernet because it is nearly four times faster than wireless.
     OS X Mountain Lion - System Requirements
       Macs that can be upgraded to OS X Mountain Lion
         1. iMac (Mid 2007 or newer)
         2. MacBook (Late 2008 Aluminum, or Early 2009 or newer)
         3. MacBook Pro (Mid/Late 2007 or newer)
         4. MacBook Air (Late 2008 or newer)
         5. Mac mini (Early 2009 or newer)
         6. Mac Pro (Early 2008 or newer)
         7. Xserve (Early 2009)
     Are my applications compatible?
         See App Compatibility Table - RoaringApps.
     Am I eligible for the free upgrade?
         See Apple - Free OS X Mountain Lion upgrade Program.
     For a complete How-To introduction from Apple see Upgrade to OS X Mountain Lion.

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Paul,
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After you install Snow Leopard you will have to download and install the Mac OS X 10.6.8 Update Combo v1.1 to update Snow Leopard to 10.6.8 and give you access to the App Store.
You can purchase Lion by contacting Customer Service: Contacting Apple for support and service - this includes international calling numbers. The cost is $19.99 (as it was before) plus tax. It's a download. You will get an email containing a redemption code that you then use at the Mac App Store to download Lion. Save a copy of that installer to your Downloads folder because the installer deletes itself at the end of the installation.
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1. iMac (Mid 2007 or newer)
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3. MacBook Pro (Mid/Late 2007 or newer)
4. MacBook Air (Late 2008 or newer)
5. Mac mini (Early 2009 or newer)
6. Mac Pro (Early 2008 or newer)
7. Xserve (Early 2009)
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Am I eligible for the free upgrade?
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4. DVD drive for installation
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Updating to new operating system from circa 2008 OSX

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