Keel Bolts&Caulking/ Advice please

[Swimpy]

We've had the '64 Connie (46') on the hard now since late April Making extensive planking repairs. Looks like we may get to splash latter part of Oct.

She is completely dried out. We are currently digging all old 4200/5200 out of seams and exposing cracks 1/8" to 1/4" wide. Everyone here at the yard says this is the proper procedure. Dig them out, apply bottom paint, then recaulk. (i'm using 4200 fast cure.) When planks swell any excess caulking will squeeze out. It was recommended to paint first then caulk so squeeze out wouldn't break paint film.
Do you guys agree?

Now on to my biggest concern.
My keel bolts are extremely loose. Should i just barely snug them now or leave them be and tighten a couple of weeks after launch? Also she has 3 struts on each shaft. i am afraid to just ignore these because of potential leaking. I don't want to open a huge can of worms by completely taking the struts down and rebedding them. The line up procedure would be nightmarish.
Can i dig as much compound as possible from between bottom planking and strut, then refill with fresh compound? (again 4200 fast cure)

Thanks Guys