I come from a similar background as you, trying to make a good living at this sport for as long as possible. Back in my day there were some that chased big races, and a few of us that chased longevity in the pro side, so looked mostly at things in a financial sense. So my recommendation is that you do the same.
So with that in mind, yes you would probably place higher in the Pro series, but I would imagine make less money. Not being privy to the contracts(but I think I know pretty closely what they are) your best net at the end of the year is probably the T100 series. Maybe someone here can elinghtn me as to what expenses are paid in the Pro series(travel, hotel, meals etc) if anything. I know it used to be nothing and everyone was responsible for their own stuff.
I believe in the T100 series a lot if not all of that is covered, and over so many races that is no small amount, so has to factor in your calculations. Also not knowing your sponsorship bonuses, you have to factor those in also. I know when I did my contracts I was able to point most of my sponsors in the direction I wanted to go, and not really dictated to me without my input. So once you do choose, that is another avenue to maximize your earning potential.
The nice thing with the T100 is you start out the gate with a nice big number, get expenses paid, so all earnings are net. You dont get that in the Pro series, even though you might actually be more competitive there. And as others have stated, we are not long for the time when a 70.3 is going to be basically as competitive as a T100, like the WC we just witnessed.
And going off of what Barnaby did this year is really more of a head fake, I can guarantee you it will not be so easy next year. I expect the fact that a low level pro was able to make more money in that one series than his entire 20 year career will wake up many to the possibilities.
So keep working on your swim, get within that 3 minute gap or under, and work your way to the top 5 like you did in many races this year. Having to do more races will be a good thing for you, many will not be able to handle that schedule, and or try their hand at the pro series or individual races in that series. It also wont preclude you from some other races, maybe pro series ones, or Roth and other big pay days that get between the T100 races. Remember you can miss some of them, so bank early ones like you did this year and your schedule opens up mid and late season for this type of thingā¦
Good luck with your decision, this is what I would and did do and was lucky enough to have a 15 year pro career. So many chase that Kona dream, but in reality virtually everyone falls short and it is a big expense, rather than a payday.