Not trying to rain on anyone's parade here, after all squads are in fact the way to go if you want to learn fast. However, i just thought i'd give you another perspective. What if you can't make regular squad appointments?
The solution exists, it will just take a bit longer to learn things. As mentioned before, try to stick with one aircraft initially. Start with a plane that has forgiving handling. Don't fret about top performance or big guns just yet. Fly a lot of quick missions to get a hang of things and then progress to a better and slightly more demanding aircraft that you can handle. This is your ride for the first few months.
Once you get there, go to mission4today.com and download a few user-made missions or an offline campaign for this aircraft. While the AI is no substitute for real human opposition, good campaigns tend to be tailored around what the aircraft can do well and this will give you an idea on what kind of jobs your chosen ride is better used for.
After you get your hands dirty with that and you're feeling comfortable taking on the AI, jump on hypperlobby and find a server that features your chosen aircraft. For example, if you want to fly a wildcat try a pacific server, if you want to fly 109s try a server that features maps from the mediterranean, european and eastern fronts.
I recommend full difficulty servers if you can manage the initial frustration. They are more unforgiving but you also tend to learn faster. I only fly online occasionally and i find i have to re-learn some things every time i start again. On a full switch server, that's about 8 hours of stick time for me to go from "where did he come from? i'm dead again" to "i have an idea of what's happening and can score a kill or two".
Another thing in favor of full switch servers is that they tend to have more team-oriented gameplay and reasonable people frequenting them. You'll still come across kill stealers and people who fly with reckless abandon, but when the aim of the server is to complete the mission and not just rack up kills it's safe to assume they'll be less.
After 2-3 evenings of flying there you'll get an idea about who the regulars are. Try to use voice communications (a lot of servers provide their own teamspeak server) and initially just listen (ok, you don't have to be completely silent, you just have to be brief and accurate so that other people can talk too, you get my drift). By saying listen i mean to pay attention not so much to what's being said, as much as to how it's being said. Experienced pilots can announce numbers, altitude and location of the opposition in a few words: "5 bandits, angels 20 plus, grid bravo delta one zero, pad/tac/keypad 1, heading west" means that he can see 5 aircraft that are positively identified as enemies (unkown contacts are called boogies), flying at more than 20000 feet, in map grid BD10 and heading west. As for the "tac 1" part, since grids on the IL2 map are squares with a 10 km side, online pilots found a way to further divide them in sub-grids. The way this is done is by looking at your numeric keypad on your keyboard. If you are over the center of the grid square, you're at tac 5, if you are over the north-eastern part of it you're at tac 9 and so on.
Read the mission briefings so you know where the action will be, follow your teammates there (or go to where they said the action is after you're comfortable with the lingo) and stand back. That's right, stay on the periphery of the fights a bit higher than the altitude the killing's happening and observe.
This does 3 very important things for you: 1) you're not getting in the way of anyone while learning and you score "nice guy" points with the veterans, while 2) you are in a position to clear their tails if they need help, getting the satisfaction of being useful to your team and scoring your first kills, all the while 3) learning how to fly cover for someone more experienced and also getting to learn by seeing how they go about the whole deal. The last one is essentially learning how to be a good wingman. One thing leads to another and after 2-3 sessions you'll have a few people you can regularly team up with on that server, regardless of not being a member of a squad.
Squads are great if you can schedule the time to attend the events and different squads have different attendance standards. If you can set some time aside weekly and you're sure that you can attend, then it's definitely the way to go. If on the other hand you're like me and you can't schedule things even if your life depended on it, i hope that my experiences will serve you well in your efforts to find people to team up with while still being a "freelancer"
