Most kids are pretty adaptable and resilient. Life and development continue while traveling. For example, when my son was 12-months old, he walked on his own for the first time in an airport gate area while awaiting another flight.
You and your LO will likely be fine. Our 2-1/2 y.o. has flown over 50,000 miles and has generally done well. The most difficult flights for us were the ones that forced him to be over-tired (not red-eyes per se; but, more like evening and afternoon departures that forced us to keep him up well past his bed/nap-time before boarding). We found the most difficult age for our son to travel was roughly 10-20 months.
MommyPoints thinks it is a similar range.
It has been very helpful for us to be prepared with different toys/entertainment options to keep his interest. As he got past the 2-year mark, his attention span has grown, which has made keeping him entertained/occupied on flights much easier. Sometimes, though, the options we brought paled in comparison to those he found himself on the plane - at 10-months, during a short hop, we spent the whole time playing with the safety briefing card and during his most recent flight, our 2-1/2 y.o. kept himself pretty occupied during a 2-hour flight simply looking around the airplane, looking out the window, asking lots of questions, and eating snacks.
So, with a 2+ y.o., I wouldn't hesitate to take both trips!