What I did when I didn't start with guitar skill was to ignore Sasha's practicing (and the upper floor) until I had the skill and guitar. I had to ignore her practicing for a bout a week or so of game time, but I eventually had it.
As far I can tell, you don't need the guitar (yet) to join the band. You just need the guitar skill. Probably an oversight. But it is quite expensive, so I imagine that you'd be stuck avoiding the event for quite some time on hard difficulty if it does become necessary. As a compromise, allow for 'borrowing' studio equipment for practice, but require the guitar for the actual Battle of the Bands.
I tend to go with Martial Arts to start because that seems so much more difficult to obtain. I also tend to go workaholic so that I can get the money and stats I need quickly.
Martial Arts is cumbersome to acquire, but it can be done. Just need to buy a bike and a swimsuit to unlock the beach, and then go 5 times to the beach (first and last time you have to be there at 10:00 to do the introduction / graduation as well as the training). It does require some careful planning though. But there are not that many useful skills in that questions to pick (Shooting is the most useful one that can't be obtained by other means, and that only affects Aletta's side story as far as I can tell). So that is not a bad pick.
Video Gaming is worth about $45 / week, if you go to the arcade on Wednesdays. It is also needed for one of Bree's paths, and the last event (unless more events have been added to that in the recent update) of the Gamer path can also fire when you are not on that path. That path is not developed to the same extent as the maid path. Probably for practical purposes Workaholic is better. Quicker promotions also mean you can start with the office characters a bit quicker, and since some of those story lines are long, speeding things up just a little bit will help.
Edited to add: It seems impossible to trigger the office party in the first week of the game (by picking workaholic, and working your butt off on Monday and Tuesday getting promoted twice in two days, since Aletta does not show up in the office on Wednesday (even if you can get the opportunity to chat with Aletta after you have picked 'Work' / 'Work Hard'. According to the event requirements, it should be able to fire on Monday, Tuesday or Wednesday, if the other condition is met. Confirmed that if: "girls_conditions": {"aletta":{"valid": True}}," is removed from the script for the office_party_set_up event, it can fire on Wednesdays. Maybe something for
Andrealphus to look into. Either it has to fire on Monday or Tuesday only, or the girl_conditions should be altered.