This is right up my alley. I've been flying R/C airplanes since 1983 with about a ten-year layoff that ended five years ago. Whew, where to start?
First thing is, you'll want to find a local club if at all possible. Very few who attempt to teach themselves to fly succeed and if they do the cost is almost certain to be high in terms of crashed airplanes and rebuilding. It can and has been done but it is much more difficult than with an instructor. The new foam models are much easier to repair than stick-built balsa wood. You will almost certainly need membership in the AMA (
Academy of Model Aeronautics) in part because insurance comes with the membership. I've never heard of a club that didn't require AMA membership. Finding a club is easy; the AMA has a "
club finder" link on their web site.
The web site
RCgroups.com is huge and can be a bit overwhelming with the volume of information available there. I'm there frequently and have found no better source of information.
Before spending a lot of money it may be best to contact a local club and find out what brand of R/C gear most of the club members use. This makes it easier to get help, and some of the R/C stuff available now can be intensely complicated. Lots of options/choices = complexity. Regardless of the brand of radio you get I'd recommend at least an 8-channel transmitter (or "control box") because you'll quickly outgrow anything less. The extra channels allow different setups and options such as flaps, retractable landing gear, lighting, "flight modes" and so on. Also look for one that has memory for multiple models, the more the better up to about 200 or so. And yes, some guys do have than many! It means being able to switch models without having to reconfigure the radio system every time like we used to have to do.
A simulator is an excellent way to start but I don't know of any that run on a Mac. That said it certainly is not essential. Many if not most of the trainers available now have settings that limit their angles of bank and pitch, some even have GPS and will "return to home" and automatically land where they took off! If you have a club instructor I would not recommend spending the money for those options, you won't need them.
Here are a number of excellent trainers to browse through, but I don't recommend buying any until you talk to a club instructor - they may have a favorite and really, no one makes a bad one anymore. Well, some in China are really bad.
https://www.horizonhobby.com/airplanes/by-type/trainer/
Horizon Hobby has what I believe to be the best product support in the industry but there is a price to that. There are cheaper places to buy but most are in China and their product support is slow at best and frequently nonexistent.
I do not recommend a "jet" to begin with which is really an electric ducted fan. It's expensive and is there only because so many people wanted one. They are fast, and that is not what a student pilot needs. There are cheaper models than those shown, but about $140 seems to be the bottom of the price range unless you're buying used gear. The Air Force does not start students in fighter planes and you shouldn't either. One that looks like a J-3 Cub is much more likely to be a successful trainer.
On electric vs. glow engine or gas engines: I fly exclusively electric now as the performance is equal to fuel-powered and sometimes even better. They are much simpler to deal with, starting, and maintenance. I'd highly recommend starting with electric for the simplicity of operation.
Off the top of my head this should keep you occupied learning for a while. Don't hesitate to ask if you need more information. Also look on youtube, there is enough there to keep anyone busy for months if not years.