It certainly is possible and is much more likely during the non-rainy months. We stayed at Pop this past Feb. and loved using the skyliner and 0 issues.
Having said that we also stayed on the skyliner one Aug. and it was pretty terrible. It was beyond frustrating because it went down so often during our trip and agsin the biggest issue is that Disney just does NOT handle it well when it goes down. In my opinion if Disney transportation is a priority to you; I would not stay on the skyliner during rainy months, just because I feel like you're setting yourself up for failure. As much as we love the skyliner, after that Aug. trip we had, we won't return to a skyliner resort for our summer trips. Now, I know there are plenty of ppl. who are way more laid-back than me and much more just happy to be on property or who are happy to pay for ubers etc. so for them it probably isn't as big of a deal, but if someone is considering staying at a skyliner resort, prefers to rely on Disney transportation then I think it's important for them to understand the reality of what they're paying more for. The skyliner is awesome and our preferred mode of transportation...when it's working correctly, but when it's not it can be very frustrating.