1 Caulk if it looks bad

2 A job can last only as long as the old paint , depending on its
condition. It can last 30+ but will look bad alot sooner. Prep and paint
and the painter are key, as in a clean surface, paint in shade not a hot
or soon to be hot surface in sun. and not when above 85 or so. Use the
best paint.

3 Spraying is optional , it will only look as good as the surface. A
pro will brush after rolling, so no roller marks.

4 Painting will take as long as it does depending on prep and weather,
you have a small house

5 Putty will flake off good caulk should not, it is a matter of looks.

6 On an old cracked surface 2 may be better for hiding imperfections but
is not mandatory, depends on job.

7 Prime bare wood only and with slow drying old fasioned oil. If
surface is chalky clean it good and only one paint made is designed for
chalk adhesion it is made by Sherwin Williams and is expensive, but
quality paint is.

8 New paint will only look as good as its surface, Gloss should be
sanded for good adhesion

*8600 for a 1600 sq ft house, alot, but we cant see the prep needed. 2
yr warranty, a joke, 7 yr that is better
Go look at their work, talk to customers