Best Upgrade Strategy

Currently on 10.6.8 and have resisted upgrading because it runs great and handles Quicken 2006 For The Mac and several other programs that I use frequently. Now it looks like I will have to upgrade to 10.7 or higher just to use Turbo Tax this year. If I am going to upgrade, should I go all the way to Yosemite or one of the interim levels? Have read so many bad reports about some of the interim upgrades.
Will also have to find out the highest OS that Quicken 2006 will run on, which will probably also be a limiting factor. If I do upgrade the OS, I will be able to use the new Quicken 2015 for  the Mac but will have to find a copy of Quicken 2007 or later to convert files for the Quicken 2015.
How did I get in this mess? (I know, failure to stay current but Snow Leopard has been such a great system). Current hardware:
iMac 27" Model 10,1
Core 2 Duo 3.06 GHz
8GB Ram
Any thoughts would be appreciated.

Eric Root wrote:
You will have to contact Intuit directly to get a copy of Quicken 2007 for Lion (10.7) and above.
The procedure to obtain Quicken 2007 for Intel (Snow Leopard, Lion, Mt. Lion, Mavericks, Yosemite) for $15 from Inuit:
Go to this page:
https://quicken.custhelp.com/app/contact/plvl1/win
and use the chat feature for Quicken for Mac: Quicken 2007 for Lion: Shopping and Buying: Buying Quicken
Once installed, be sure to check for upgrades (current version is 16.2.0)
It will open your Quicken 2006 data file directly.

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