15 years ago I thought the idea of buying a guitar online sight unseen (or unplayed) was lunacy. Now the majority of my rather expensive guitar purchases have been online.
The reason I have more confidence in doing it online these days is that I'm confident in what I know I want from a guitar. Do your research, know the model, know the specs, scour forums and reviews, watch youtube videos about that particular guitar - or as close as you can get to it. By the time I order I have a pretty good idea of what that guitar is going to sound like, and a reasonably good idea of what it might play like. There is some unknown involved, sure, but you can usually get a pretty good sense of these things by doing your homework. I've bought both new and used guitars online this way and I've never been disappointed. I've even asked Reverb sellers to weigh a guitar for me if they haven't listed the weight in their description because that's something I know is one of the key determining factors whether I will enjoy it or not.
I will add the one caution that you need to do a setup on the guitar after it arrives BEFORE you make a judgement on whether its good or not. I've had a couple arrive and kinda felt "meh" about them until I did a full setup and got it playing the way I like. THEN it was like, "wow, this is awesome!" You'd be surprised how just a 1/4 turn of the truss rod and setting the string radius and action can take a guitar from 6/10 to 10/10.