Hi Brenda. As mentioned in my post, I'm a dinosaur when it comes to software. In my case, I was going from Q2000 in Windows XP to a new Windows 7 computer. To retain my original files I had to first download Q2004 to both computers, do the transfer, and then download Q2013. So, by inference, you shouldn't have a problem making the leap to Q2013 from Q2008. The one caveat, which I didn't realize until I read a few of the Amazon reviews, was that by ordering the Q2103 Starter version I may have complicated the transfer of historical files. I don't know this for certain but one Amazon reviewer suggested the transfer of existing data works best if you purchase the Q2013 Deluxe version. Hope this helps. Good luck.
Should be no issue ... my upgrade from 2009 to 2013 was very seamless. The upgrade program recognized the Quicken file, pulled in my data and converted to a 2013 file with no issues. Be sure to back-up your file first.