No problem!
Your first point is one reason that I'd reccomend 'fingerstyle', because I've personally found that you can play 'the beatles' with higher fidelity with one guitar using that technique, than with a pick on steel string, simply because transcriptions for fingerstyle expect you to imitate both rhythm and melody aspects - this is true of rock and pop music. You can't play Blackbird by strumming chords and have it sound good enough that you want to play it, and while you can't get the exact studio sound from one guitar, you can get a lot closer with 'fingerstyle'. Even duets, like Dire Straits Sultans of Swing (I think is two guitars I might have the wrong one) can be somewhat accurately produced on one guitar with fingerstyle, compared to the alternative. Of course, it will always have the usual 'nylon string' sound, but again, starting from nylon means you can fingerstyle on acoustic (for limited periods at least before it hurts too much). In the case of songs that are just chords, you can with fingerstyle technique turn them into something more complex and interesting. I've found that singers find being accompanied by fingerstyle somewhat easier too, since it often gives better note and timing cues/calibrations, compared to multi-note rhythm chords.
I see what you mean about elitism, I should clarify my terms - while the nylon string guitar is called 'classical', really I don't mean 'classical' music, there is a huge range of music that isn't 18th/19th century orchestral pieces that is commonly played on nylon strings, such as Spanish, Portuguese, Balkans, Greek, Irish, and so on, more kind of 'folk' music, not so much the conservatoire of the European elites. And even with traditionally 'classical' in the common sense of the term, theres a fair amount like the Baroque period, or Bach for example, written for Lute (which is very close to nylon string guitar). And also, as I mentioned, replicating piano or even violin and wind instrument pieces is easier with fingerstyle than with a pick. Its more accurate to describe it as 'fingerstyle', and I do think that broadly speaking its a more versatile method than using a pick and an acoustic or electric, since those are recent inventions and we've been using 'fingerstyle' for a lot longer.
Yes, I mean the 'acoustic' strings exactly, they're harder, but also a nylon stringed guitar has the strings and frets placed further apart (to accomodate fingers rather than a narrower pick), and there are some other differences in the neck and other pieces, all of which are tailored to the style. You can play fingerstyle on an acoustic but it tends to be harder not being built for the style - although I would be surprised if you couldn't find acoustics built with that style in mind, since electric guitars vary in string placement for styles, though I haven't looked. I understand not wanting to buy another guitar, but it will be more challenging to learn fingerstyle without a nylon string. However, there are players who produce very complex results with picks, it isn't necessarily such a barrier, or combinations of picks and thumb (for the bass line), and also finger attachments you can buy that are essentially plastic nails so that you can pick on a steel string (though again, string placement will make this more difficult even with such picks, and it also is a style in and of itself to learn).
In terms of keeping up motivation, I acquired a wide range of different materials, including transcriptions of music styles that I was a lot more into, but also including those that I wasn't so into in terms of listening, so that if I got too bored I could switch to an entire different style. I'd reccomend (again, budget permitting) getting materials for jazz, pop, rock, folk (of differrent kinds and traditions, like Spanish, Samba etc etc), classical 'elite', and so on, becasue 'variety is the spice of life' and it both helps you improve and keeps interest up, and even a favourite song will get tedious if its all you know or play. I also didn't treat it like a kind of structured or targeted thing (some of my favourite songs I can't play on guitar, because I can't find good transcriptions or because a single guitar just can't replicate them), or give myself particular goals or times, but that does work for some people. Its sort of different enjoying listening to something vs playing it sucecssfully - sort of like if you hate watching golf and even the idea of it, you'd still be pleased with yourself if you learnt how to get a hole in one or whatever its called. Or even if you hate soccer, but you learnt how to do a backflip kick and score with it. Or if you find sculpture fundamentally boring, but learnt to produce a lifelike bronze horse or something. I suppose I'm interested in the process/mechanics/technique, so that I don't mind so much what the aesthetics of the result is - I'll happily play songs that I would never listen to, as long as they have something interesting about the arrangement that isn't just strumming three chords if you see what I mean. But then I don't sing, which I think is where it becomes fine to just strum chords, because you've got two instruments so it can be more complex.
I think fingerstyle helped me keep up motivation, because of the wider array and complexity of the techniques being learned, compared to strumming which I started with but was hard to keep interest in, like I said because its harder to reproduce music satisfactorily, and also because there is a limit (to a degree, there are advanced techniques like rhythm flamenco too) to learning once you've got rythm guitar nailed.
Music is a very good pursuit for your whole life, since you get better with age, compared to lots of sports where you inevitably decline to the point where it becomes somewhat pointless. The best players I've seen have been completely outside the music industry (either elite or pop), playing traditional music in street cafes, and have always been very old, just playing with friends.
yes, they are all quite heavy!
Its two aspects, having to press on the fretboard (individual notes or chords like with 'bar chords'), and also strumming if not using a pick. Your hands will get used to them over time either way, but lighter is better to start because it takes time to build muscle and callous. But really even if you start with lighter, and later try heavier, you'll have built up the required hands to not find the heavier ones too difficult. But if starting with heavy, to the point where you can't even comfortably press hard enough for long enough to get a note to sound, then its too heavy and you should start lighter, if that makes sense. You'd get too frustrated if you had to put too much effort into pressing a string, it'd slow everything down.
edit: I should add, that for me my occupation helped a lot since I use my hands a lot, but from your other comment, I'd expect a computer based occupation would give the dexterity & speed, with some adaptation, but the muscle development required would possibly be different. There are finger strengthening exercices that would help (you can find online), or I'd expect another simultaenous hobby that requires you to use your hands would also build that. If the strings are difficult to press to the point of it getting in the way of learning either go lighter, do exercises, or (as elsewhere) nylon strings are easier.