***** NOT A TEACHER *****
Good morning, Will.
May I answer your first question?
(1) According to Dr. John B. Opdycke in Harper's English Grammar:
(a) A phrase such as "a too large crowd" IS grammatical but definitely NOT idiomatic (the way native speakers use the language).
(b) Dr. Opdycke says that the following sound awkward and ridiculous:
a so sweet story/ a too severe strain / a how excellent view.
(c) He says that sound is the deciding factor in such idioms.
(d) Therefore, I think that all native speakers would suggest that you say (and write) ONLY: too large a crowd/ so sweet a story/ too severe a strain/ how excellent a view/ many a boy. ...
Have a nice day!