The latency hit of the extra trip will definitely be felt by end users if the endpoint is far enough away (e.g. ~100-200ms.) You can mitigate the initial setup other ways though, like the CDN approach: terminate TLS much closer with a proxy and use a warm, pre-established backhaul connection to the origin.
Less round trips are always good, though, without any extra stuff to put in place.
Less round trips are always good, though, without any extra stuff to put in place.