The money spent on coaching will get benefit you far more than any money spent on high end gear. A couple of years ago, I would have laughed at the possibility that I would ever race at my current level. Many triathletes are type A and need someone to reign them in more than someone to motivate them. Having someone tell you when to work hard and when to recover is crucial. The team I race and train with is spectacularly competitive and I believe that it has as much or more to do with careful coaching than with talent.
The key is to have a coach who will create a realistic training plan that fits YOUR life and your commitments in the real world.
Until the last year, I mostly trained short course, but my coach is a long course specialist with somewhere around 20 Ironmans under his belt and 6 or 7 trips to Kona. I have seen amazing improvement in short course over the last couple of years and had a smooth tranisition to long course this year. He trains both elite and age group athletes and all of us are everyday people balancing school, work and families (I am a medical student). He is San Diego based but has online programs as well. PM me if you are interested.
Lets be honest, while all of this training is fun regardless, who doesn't want to see results for all their hard work.