Wow - you are like me! Lots of goals. But you can make them work.

1. As someone mentioned, you can break your year into training "blocks" with different emphases during different times.

2. BIKING HILLS. Do you live in an area where you can access a lot of hills? I've had ITB problems running, as well (especially running/walking downhill). Biking UPHILL has really strengthened me for running, including running DOWNHILL. My guess is that strengthening the quadriceps is what helps. Anyway, biking hills will help you with 3 goals, (a) becoming a stronger cyclist, (b) preventing injury when you start running, and (c) general strength training.

3. For strength training, do all the research you can and focus your regime on targeting muscles that are weak or inflexible FOR YOU. For instance, I have a tendency to get hip-flexor strains while running, so I focus on adductor/abductor strengtheners as that is supposed to help MY PARTICULAR problem. There are so many ways to do strength training; you may as well have it focus on your personal limiters. In my case, a single visit to a PT helped to identify my muscle limiters and specific exercises to address them. I can do strength training at home, twice per week x 15-20 minutes and I'm done.

4. Running. Running injury-free requires a couple of things, (a) frequency and (b) building up your distances very, very slowly. At some point you'll need to make a choice about whether you would like to "run" your triathlons, or whether you are satisfied walking them. If you'd like to run them, then the key is to start running really often, 3-4 times per week at least, for several months prior to the race. We are talking 20-, 30-, 40-minute runs, nothing too outrageous. This frequency and gentleness will set you up to be injury-free. If you are not into running then it might be a good idea to just bag it right now and say, "I'm just going to walk those tris." If however it sounds even remotely appealing, then yes lose some weight first and then gently take up the running. An advantage of running is that it is ridiculously time-efficient compared to the other sports. Lace up your shoes, go out the door, back in 30 min., way more efficient than going to the pool or the gym! Also, it is a GREAT calorie-burner. I tend to lose weight the best when I'm running.

good luck!