well you didnt list if you have specific performance goals or if you just want to finish/enjoy your first HIM.

Good point.
Basically. The two early season goals carry my highest performance goals.
I have podium goals(clydesdale, not ag) for both of them.

For my half ironman I really just want to be trained enough to finish actually running, and with a smile on my face. Not crawling.

I guess I'm answering my own question here.

The real question should be more like.

Is 11 weeks enough time to build from an Olympic distance race to a HIM?

If I were you, I would do #2: setup your entire season around the fall HIM. You will probably find that if you train for an HIM, then excellent performance will just happen organically for your sprint and Olympic triathlons. That is how it worked out for me. I just finished my second season. My effectively first triathlon was an HIM in April 2016. I started training from a running base in December before the race. After that race, I continued building for a second fall HIM, and I did a sprint along the way. I easily won my old-codger AG in the sprint with no specific training. I was self-coached and pretty much used a Kurt Kinetic Road Machine and its free app for nearly all of my bike training. I only got TrainerRoad in the late summer, just before my 2nd HIM.

Those half marathons will be critical for you, because it seems like you do not have a strong running foundation. Those will be significant confidence boosters. Then add to those some long rides (60-80 miles) and some bricks as the HIM nears. Those should give you total confidence in your preparation to let you finish with a smile.

I agree with the above post. The training should be geared around your HIM (A+ race), and the others you can use to build confidence and experience.

However, I find that once you start crossing into HIM territory, then nutrition becomes a much bigger piece of the puzzle for a successful race execution. Most people can do sprints and Olys on just a minimum of sport drink and/or gels, but once you start increasing to 4-5 hour efforts, you need to have a nutrition and hydration plan. Use the season (and the Olys) to figure out what you can stomach and still run effectively.

I also agree with a 1/2 marathon and a longer bike ride (at least 40-50 miles) outside at least once prior to a half IM, and I say that as someone who trains on a smart trainer 99% of the time.

Good luck!

Likely yes -- really only difference will be stretching your long run and long bike. Mostly you want to be able to get 3+ hours of saddle time and 10-11 mile run in (~80% of 13.1) to comfortably finish from a fitness perspective.

The real difference is nutrition and hydration -- you can "fake" your way through an Olympic but Half Ironman you need a strategy (and training for it). Easy to train for -- just focus on race nutrition in the long bikes/runs. That is going to be the biggest factor of crossing the finish line with a smile.