Frankly the Maya + Josy back story is full of holes. Nevermind the long distance relationship, how did they even meet, or associate closely enough to start one, which is implied to have been at least a conventional one(i.e. not long distance) for a time.
Josy has lived within biking distance of the MC for years. Long enough that she's gotten to hate Tommy, who would have been mostly away at B&R for at least 3 years by story start. That they didn't know each other at least peripherally until going to the same summer job breaks my SOD. Their home town is small enough that the nearest 'small college' and one with a slim selection of courses at that is a train ride away. They should have gone to the same high school. And the town seems remote enough that everybody would know of everybody else his/her age even if they don't ever interact. Including social pariahs. If only for the fact that even a relatively small population would have a pariah.
Which brings us to the actual relationship itself next. How did they even meet? Maya is implied to have gotten flak from her dad because of her relationship with a girl, presumably Josy. Except that just runs into Josy having lived in the same town as the MC for the past several years and Maya herself having mostly lived with her family several hours away.
Isn't that a lot of assumptions on your part? I live withing biking distance of thousands of people I don't know, and it's mostly a rural area. Sure, I know many people there, but the vast majority I don't know, including some of my closest neighbors. And where did you get the idea that they only had one school!? I'll go play once again and try to pay real close attention, to see if I spot any information on that regard. It's easy to get distracted by other things in the game!
About Josy and Maya living relatively far from each other and still knowing each other, and ending up having a relationship: I don't see a problem there, either. I've met some of my friends while away from my area. In some events like sport competitions, concerts, conventions, etc. And have you ever heard about the internet!? You don't really need much imagination to find ways where they could have met. Plus, they could have met through their parents or whatever. Imho, it's much more restricting assuming they should only know people nearby.
And don't confuse lack of information for it being a plot hole. If Dr. Pink Cake explained every little detail, you wouldn't have much space for using your own imagination, nor would there be any mysteries. And the volume of redundant and irrelevant information would make it a really fucking boring game, imho. I'd rather prefer the attention focusing on the main plot and the character relations, and the veil over the mysteries surrounding the characters being lifted progressively.