I do want to remark briefly on what is admittedly a minor point that you made, namely that triathlons are highly recommended "... even if just doing sprint/olympic/half distance." It is a common misconception that the longer the distance, the more difficult or meritorious it is to complete. However, this is not true: It is not the case that one races an Ironman at the same intensity that s/he would for, say, a sprint-distance triathlon; rather, in order to last the entire duration of the longer distance, s/he is racing less intensely. (A person who performs a sprint-distance triathlon at the intensity s/he can hold for an entire Ironman is not racing the distance.)
Let's go to running for a concrete example. A topnotch overall pace in the marathon is 4:50/mile. But a miler will run a single mile in 3:50, a whole minute faster than marathon pace. (Note that these are typical competitive times rather than world-record times.)
With all this said, I would be remiss not to say that I agree with the overall sentiment that one should take baby steps rather than brashly pursuing unreasonable goals.
In response to your final question, I haven't done triathlons since college. At the moment, I am working on getting into shape to finally break 5:00 for the mile run. Next up is breaking 1:00 in the 100-meter swim. I'm still figuring out what a reasonable goal is for cycling... maybe 5 miles in 10 min.?
After I have all the pieces, I'll put them together and start doing triathlons again :-).