I’d probably take option #2, but is this the only vendor available? Actually, the real question I have is why it has to be a specific clone of Red Maple? I could understand if it was a dwarf or fastigiate form, but this one is neither. I’ve never had the pleasure of experiencing the dictates if a HOA, but this seems so arbitrary.

Yes, I agree with you. In fact, getting their "permission" to plant a tree in a communal area took over a year of filling forms and sending emails. Then the "community arborist" recommended this particular type of tree. So yes, it is arbitrary, but It it is what it is. I am determined to plant the best October Glory Maple I can find!

On the other hand - why would you go for option #2?

My thinking on picking option #2 is it will likely be less root bound, easier to handle, and faster to establish. This is somewhat subjective since we’re making a decision based on a picture.

Agree I'd opt for the least rootbound potential. They all look 'telephone poled' in the containers so also check for possible girdling roots and plant it correctly.

And once it's home and out of the pot, here's a quick video on how to deal with pot bound roots before planting.

https://www.youtube.com/Univerity of Minnesota:

Buy the smallest one possible. It will grow the best and faster than the big ones. Look for the best leader. You want one with one main leader. Here is a photo of my Red Sunset. It is a cousin to the one you want.

The October Glory has more orange, green, and yellow. Red Sunset has more red. Mine looks like that as it starts to turn for a day or so. Be sure to keep the root flare above ground.

Pennlake is right, those will certainly be rootbound. Need to take them out, wash the soil away, and cut and untangle the root mass. Alot of work, yes, but necessary for that type of potted tree. Very poor nursery practice to make that necessary. To be honest, I'd order a small, bare-root one. There'd be little difference in size after 4-5 years.