You sound like a cool dude, soulpatch, and I'm sure you'll be fine. You've got two things going for you as I see it.
1.) Age and maturity. Most stupid behaviour and the serious accidents that follow are by young guys who let their ego get the best of them. Kitesurfing is a bit strange in some ways. Whether you're on a twin tip or surfboard, It's probably the easiest water sport to take on in terms of learning curve (wave surfing and windsurfing are much harder to learn), but at the same time it can be by far the most dangerous. That's not to say other water sports won't get you killed, but the time it takes for a 'kitemare' to go from bad to worse to potentially fatal is only a matter of seconds. Most riders that I would call "dangerous" are young guys who've have had some success, they become over confident and then hurt themselves or someone else. It really sucks because a lot of these guys then drop the sport completely and/or they give the rest of us a bad reputation at our local spots. Nothing pisses off the regular crowd more than a beginner behaving like a dummy when they should know better. I think this is a universal mindset among regular kite surfers.
2.) As mentioned in another post, you're already a surfer so you're miles ahead of most beginners. Flying your kite is the easy bit. Once you've got that down as second nature and you can focus more on your board you will experience massive improvements, I have no doubt about that.
There's lots of great advice on the thread already so I won't be repetitive, but to say, it is always a fine line between challenging yourself to develop vs. creating problems for yourself. You're obviously the best judge of what's appropriate for you and when to try new things but my best advice is to become self-sufficient as soon as you can. I'm also out there by myself quite often because it can be tough to get all the stars aligned so a group of friends can get together for a session. Real life commitments, forecast, etc. etc...
As far as the self-landing goes, well, I have actually practiced that quite a bit during my lessons.... my instructor has me set it right on it's side and shortening up the high side to dump that leading edge right into the sand or water.
While this is the method I use 90% of the time solo understand that it wont always work and went it fails the kite powers up very hard and loops hard in to the ground on your other side. It's great in 8-20 knots but above that it starts to fail.
Honestly, I'd rather never self-launch but the reality of my situation is that if I don't I am really going to limit my time on the water just due to how my life is currently.
I would probably only get 1/2 as many sessions if I wasn't willing to self land/launch so it's something that is super useful to be competent at.
If I could choose though I'd rather self launch every time if I never had to self land in over 20 knots.
The most important thing for self launch is that your kit isn't messed up before you start to rotate the kite, because once you start, there's no stopping.
I always rig directly downwind when self launching and do a visual check of all 4 lines. Then grab the lines as high as you can reach in one hand and hold your bar in your other and walk in to position while holding the lines up high.
You might find yourself in over 20 knots just by bad luck or bad forecast. Knowing how to self land by simply releasing to the leash is critical, so having practiced that you are in good shape. When around 30 knots, might be best to do it in water, as that dampens the chance of some kind of re-flight. In either case, make sure the kite has turned over so that it is sitting on its leading edge, not on its back, before working up the single flagged front line.
I self launch and land all the time. You just pull on one line and the kite rotates and then launches. Works great.
To land I either try and maneuver it to fall leading edge down or if that won't work or its too windy I bring it to the side of the window and do single line flag on the front lower line.
On airush kites the bridle allows the kite just to turn onto its back without power and sit there and you just walk up to the kite using the front flag line and then flip it over.
Yeah, the ol' empty beach.... well, now that high season is over and it is getting tropical hot here that is much easier, thank goodness.
Regarding the high wind issue.... yeah, I will keep an eye on that.... when we spent time in Bahia de Los Angeles at our old place there the sky was really great about letting you know high winds were coming.... you could read it like a book.... here it is a little different but I feel like I am getting a pretty good read on it by the way the clouds stack up against the Sierra Madre and the windlines outside.... but, I am learning so I will practice caution with the wind.
RadDrDuke, that is what I find works best for me, too, but I am still such a beginner I am open to all knowledge..... Put it this way, when you have my skill sets it is not possible to get worse, only better!
My last lesson was super fun..... I even had some small jumps over waves but, heck, I have to think about every single thing at this point!
I was even getting where I could control my speed a bit which made me very happy because it was all haul ass mode until I ate it the lesson before.
Anyway, it's a rush and I will keep at it and have fun and be safe with it.