Yes you can make progress on outranking authority sites with Web 2.0s, but it depends on using properties that have strong metrics with relevant content on its pages, and building them rock solid, like PBN sites. Most Web 2.0s provide weak tea links due to having low authority and being too thin (only a dozen or less pages).
Build a list of properties where the DA and/or DR is moderate or high, and create dozens of pages of relevant content, and that should move the needle. Most of those pages (other than the main pages) may not need to be lengthy, but they do need to exist to get the properties out of the "spam footprint" zone.