As a reference point, I've run many sub-four miles. My first was indoors, but I wouldn't say it was "easier" or "harder" than others. You try your best, race the competitors and run through the line. My PR was in the low 3:50's, but guess what - that was the easiest race I ran (based off of feeling).
Okay, so you're not talking about "feeling" but rather the ease at which it can happen. If you're talking about happening first - then I'd say it's the lower-key environment, the knowing/confidence that there's no wind, the intimate atmosphere that rarely any US outdoor meets actually offer and most importantly the strength athletes have indoors.
I've come to realize that I didn't need the "sharpening" that many people, coaches, trolls, etc actually think I needed. My mileage and strides got me to mid 3:50's indoors with absolutely no track work. Track work can be great or detrimental - it's a fine line. The problem is that soooo many coaches like track work, so they'll push you into it earlier than necessary. Well guess what, you're really strong and have ample innate speed, that's a better recipe for a virgin sub-four miler than a guy who's been pounding the track for months (at the coach's will) with weaker strength.
On face value, breaking four for the first time is "easier" indoors for completely different reasons than you might suspect - for those of you know what "endogeneity" means, you might understand - virgin sub-four milers might need the training and atmosphere to accomplish the standard. It's the training and atmosphere for new guys rather than the other explanations that make it "easier." Sub-four is sub-four. Don't knock how it's done...
Just my thoughts.