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There could be a couple of factors that might help decide which route to take. If 2018.x has a "must have" feature that your end users including maybe executives are looking to have then it might be worth going that route. One thing to help clarify since some folks reading this thread may not be aware. For the first six months after a release such as 10.5.0 we come out with a monthly maintenance release for the next six months. So for example for the 10.5.x branch we've released 10.5.1, 10.5.2, 10.5.3 and this month 10.5.4 will be released. Whereas 2018.1 is the newer release and it's just entering into it's maintenance release cycle. This month we'll be releasing 2018.1.1. After 6 months has passed then the maintenance releases move to every quarter *unless* a security issue bubbles up and/or an issue that Tableau feels will have a great impact on a number of customers so releases may happen sooner than a quarter. In a nutshell, the 10.5.x code branch is now more mature since we're deeper into the maintenance release cycle than for 2018.1. Though again, if users have been patiently waiting for a newer feature it might make more sense to go with the newer release. As a side note, 2018.2 is now already in its first Beta release.
Would also recommend having a look at the known issues page and can't stress enough that it's always a good idea to do some testing of a newer release in a non-Production environment *prior* to upgrading where you test at least the top 20 dashboards as well as critical/executive dashboards to make sure you don't run into anything unusual.
Upgrading to x.1 version in an enterprise environment makes me nervous. We are considering 10.5.x or 2018.2 for our next upgrade. It all depends on your company's risk appetite.