A gaggle of questions about traning from an old geezer...

Hello everyone,

After gaining by ticket in 1993 at KOAK my logbook was moth-balled and
I haven't flown again until last month. After regaining currency I
would like to try and ascend through the tiers and maybe, one day,
hold a Commercial License with Instrument rating. I currently have 85
hours logged as PIC, of which 10 are solo x-country.

Now to my questions:

1) My motivation may be a little unrealistic, in an ideal world I
would like to switch careers and become a professional pilot, however,
at 40 I'm probably too old. The airlines probably wouldn't be
interested, but could I do something else?

2) I have a fulltime job and family, so a fast-track type school is
out of the question. My current plan is to enroll with a local flight
school and fly as much as possible, however, I'm confused about the
order in which I should do things. Does it make sense to do instrument
first? I've read about combined instrument/commercial training. Should
I even worry about multi-engine at this point?

3) Regarding the required 50 hours x-country time for the instrument
rating. I am confused about the circumstances in which 2 pilots can
both log PIC simultaneously. My understanding was that one
circumstance is when PIC#1 manipulates the controls under the hood and
PIC#2 acts as safety pilot. Is this the only case or can two private
pilots log x-country simultaneously on a regular trip (more than 50nm
etc.)?

4) During training (with the instructor), how much flying, if any, is
performed in actual IMC? I ask because I would like to fly early in
the morning, and on most days, OAK is 1000' overcast until after 9am.

Thanks in advance for your patience.

SimGuy