1. The gap is smaller, and shrinking every year but still exists, and it's not just macros; the condition system and the tooling is way better.
The tooling alone is sufficient reason for me to use lisp. Even commercial IDEs for python (e.g. pycharms) are nowhere near as good as slime, plus sbcl is a compiled language. I can change a function, run a test and get instruction level profiling information. Pretty much no modern dynamic language lets you do that, and the non-modern static languages (e.g. C++) take longer to link (much less compile) then it takes me to do all of those steps for incremental changes in lisp code.
2. I have a strong simplicity bias, so I can't argue there. I will say that lisp is good at "getting out of your way" which helps remove a lot of accidental complexity. Java (particularly the Java from 15 years ago), is notoriously bad at "getting out of your way" so they are near opposite ends of the spectrum there.
3. Lisp works fine in teams; most languages with small communities have fewer team projects just because the set of possible teams grows quadratically with the size of the community. This is exacerbated in the lisp community which historically has several silos. For open source projects, SBCL (which is written in lisp) is the first team project that comes to mind.
For commercial software, QPX comes to mind; ITA was listed as having 400ish employees, I'm not sure how many were working on lisp code though.