Quicken data files from 2010 on should fully convert with no loss of data. Older data files need to go through a multistep process.
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Before any upgrade, you should have all your data files backed up and a means to reinstall Quicken 2013 should it be necessary. I would also validate your data files prior to starting the conversion. It's quite likely the validation routine will find things that need to be repaired.
If you are tracking investments, I seem to recall occasionaly hearing people complain that they lost price history for certain securities but don't recall the circumstances.
Consider the fact that the newer versions are subscription based. If you don't renew the subscription, I hear Q will take up a large part of your screen perpetually nagging you to renew your subscription or upgrade.
Others can advise the true nature of this. I am using Q2016 which may be the last year for non-subscription.
You may be able to find Q2016 on ebay or something, if this is of interest to you.
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