I've been using Vagrant successfully for several years, since shortly after it launched. It's dramatically improved the dev workflow for myself and my company.

The worst time I had with Vagrant was due to an authentication bug in v1.8.5. That was compounded by the previous release (1.8.4) being incompatible with the latest VirtualBox (5.1). Hashicorp was slow to release the fix, and we had to tell users to downgrade both tools. That sucked. This was late summer 2016.

It's been smooth since then, and I haven't had to think much about the VM aspect of our tooling in 6 months.