Yes. We've been a 2 EV family since 2013, with a variety of combination of EVs.
Our first experience was a 2012 Nissan LEAF (3.3kW charging) and a 2013 LEAF (6.6kW charging). With ranges of 79 and 84 miles respectively, both needed to be charged every night. But the 2013 was recharged within just a couple of hours and I would simply swap the plug before bed. A minor hassle, but not huge. Plus I had the 2012 text me at 9:30 if it was not charging.
Then the 2013 LEAF got traded for a first-gen Volt (40 miles of range, 3.3kW charging). This was where we ran into a problem. The Volt charged REALLY slow. Not only was it 3.3kW, but it ran its cooling system so hard that it took forever to charge. If my wife was late getting home at all, I would have to stay up late to swap plugs, or occasionally I would swap plugs at bedtime and top her off in the morning, or I would drag out the portable EVSE and charge her at 120V overnight. So with this combination, I built a 2-headed "J1772 Hydra" splitter that had two plugs. It could either charge both cars sequentially (one car would wait until the first one finished), or simultaneously--both got half power, which was fine since we had a 7.2kW (30A) host EVSE and each car could only take 15A max anyway. This made life easier.
We then temporarily moved to an apartment and only had access to a single 120V outlet, but even then we managed. Granted, hers being a PHEV meant that if she didn't get a charge it wasn't the end of the world, and I was able to plug in at work, so this is kind of cheating...
But eventually we moved to a new house. I left the host EVSE behind and rebuilt the J1772 splitter into a full J1772 Hydra EVSE (pretty much the same thing, except didn't require a host EVSE). The Volt lease was up and was replaced by a Bolt, and I traded up to a 2016 LEAF with 6.6kW charging. We still took advantage of the dual plugs, but didn't really need them like we did before. Now it was my LEAF that could finish charging in a few hours, and her Bolt didn't need charging every night anyway, so we probably could have gotten by.
Eventually I got a Model 3 and then everything changed. Now we had a car with >300 miles of range and one with ~240 miles of range. Neither had to be charged every night (more like every 4-5 days) We still have two plugs, but could easily get by with one. I normally plug my car in when it gets down to 100 miles of range (humorous, because our first cars didn't have that much range when full!), so if I came home and discovered she was charging that night, I could just wait until the next day no problem. And even if it was a bit more urgent, I could add 40 miles of range (more than a day's worth) in 90 minutes (my EVSE is still only 30A capable, so even slower than a mobile connector, much less a wall connector).
We never take two cars on a trip simultaneously, but even if we did, the planning doesn't seem too onerous to me. Just charge one up two days before and the other the night before, possibly topping off the first before bed, and again in the morning.
Having long range cars makes it easy to share a single plug at home. I would at least try it out before you commit to installing a second one.