Pre-Dominiom war when everything is pretty chill. Starfleet kinda seems fun until you realize that you have to basically do military training and all this bullshit to join and then you gotta go die in space half the time. I'd maybe just try and get a runabout or the equivalent and just sorta wander around with some pals and look at totally safe and previously explored space things. I would also open a Volcel Precinct on Risa.
geordie didn't go into that planning on falling for holo-brahms and he was incredibly down bad, and the followup episode shows professionalism and maturity in handling rejection, although it's a bit of a contrivance that he never looked at her space wikipedia article and saw she was married so half the conflict shouldn't have happened but whatever.
minuet was extra special binar computer magic.
barclay is a mental illness character and i don't think there's a all that much difference between what he did and the masturbatory fantasies people have, and there's dialogue about how the other characters invaded his privacy. He wasn't shown as creeping on the women outside of the context of the holodeck either.
Yeah, the Brahm's thing wasn't as bad as its made out to be. Except for All Good Thinfs where in that future they're married. Let Geordie find his own path and let Leah just be married, let's not fuck over a husband who for all we know is a great guy just so our main character can obtain love interest.