there's a lot here - and this may have been discussed in other posts - if I duplicate others responses my apologies.
- A "good" acoustic guitar is not particularly hard to play - at least it can be much easier to play than a "not so good" acoustic.
- I have a Larivee (OM-3 model I think) and it's pretty easy to play. Before I got the Larivee (couldn't afford anything very good prior to it) I thought acoustics were hard to play, but now I don't. I think the quality of the instrument for playability makes a much bigger difference than it does for electrics. I actually like cheap electrics. Cheap acoustics can be terrible.
- While I have a Larivee - I also thought Taylors were very nice - but Taylors are very expensive now and I liked the Larivee almost as and I could afford it.
- I tend to hit the low E string pretty hard when I play and this often causes buzz on acoustics (I have to be careful when I play to avoid it). Listen particularly for buzzing when playing. Even after a setup I still have to be careful because I play very hard on electrics, and changing to acoustics I have to consciously ease up and not
thump the strings so hard.
- I got the OM model from Larivee. It's code for "orchestral model" and it's a smaller body size than
the dreadnaught size. I liked the bright chimey tones and the ease with which it played. It's also more comfortable to play in my opinion. The dreadnaughts will have a more beefy sound but lacked the air of the OM especially with finger picking, and to me are a little uncomfortable to hug my arm around. But the bigger boxes have a great sound for lots of types of music - especially chugging strumming type songs.
- Nylon's going to sound like nylon. It's fine for some things, but you're going to be sonically limited. That's fine, but just analyze the stuff you want to play and see if needs the steel string sound. Almost everything I play acoustically needs the steel string acoustic sound.
- check craigslist to save $. Some great deals can be found.
good luck with it.