I have played with a two sting stunt kite for years, and recently this summer had some time with a small trainer kite (bar and stall line) and then a bit in the water with a harness and 8M kite. I found the kite/harness way more fun as my hands never got tired, but harder to learn as I was used to 'holding' onto the lines instead of just using them to guide the kite.

I am going to go with a 3-4M trainer, but wanted to know if it is bad to get into a harness right from the get go. Thoughts?

I am going to be focusing on mostly static this winter and summer next and hopefully make it onto a snow/wakeboard this upcoming year or next. So I would like a harness that is good on both land and water. I am leaning towards a sitting harness as it will be good for overall comfort but will likely upgrade to a waist should I start doing jumps, but am interested in hearing your thoughts and suggestions as well.

Get a harness. A seat harness is good for a beginner because it will not ride up to your rib cage like a waist harness will if you are spending a lot of time with your kite high in the window. I recommend an Ocean Rodeo Sessions II or a Peter Lynn Divine.

I would recommend a seat harness when you are ready. I would recommend that you not learn (flying static or snow kiting) with a harness and a fixed bridle kite. Much safer to learn with kite killers if you are flying fixed bridles then on a harness. If things go wrong with FBs and a harness, you need to have the wherewithall to QUICKLY drop the handles and reach up as far as you can to the brake leaders and haul them in as you likely won't have the strength to unhook and let go in an emergency.

Just my $0.02 and FWIW I flew fixed bridle kites for 2 years before hooking in and then I began hooking in on straight runs and unhooking for the turns (KLB and snowkiting).

If you are planning on getting a harness, I would say get something designed to fly with a harness. Either something that flys off a bar, or depower. The strop route for fixed-bridle kites is not for beginners. It takes time, talent, and skill to quickly drop a fixed-bridle in that position (you cannot simply let go if something goes wrong, you have to get the lines off the harness which is not always easy).

There are quite a few inexpensive small trainers that are depower. If your end goal is to kiteboard, or snowkite, then going that route may help you in the long run.

Best of luck.

There are sort of 2 camps when it comes to harness use. Those who think it is good for beginers and those that don't.

If you pay for lessons , it is their goal to get you flying with a harness and depower in the 1st lesson.

The trick with fixed bridle with a harness and learning is to hook in when walking back upwind and when you feel like resting. Unhook when you are about to do anything tricky. This will allow you to flop in and out by memory reflex + extend your sessions greatly. I still use this basic pattern of unhooking when I am about to push and staying hooked in when comfortable. Comfortable just includes cruising now. So, I say use a harness early and safely to increase your fly time as a beginer.

As others have suggested you sound like somebody that may be better off getting a depower foil. You sound like you have the basics and depower is the route you will go ? Something in about the 7m size will serve you well as you grow? Can't go too wrong getting a trainer either. Cheap way to get addicted.