How to make the best of 1-Stop flight
 

I am flying UA286 SAN-SFO-ORD and then connecting to another flight to RIC. I want to either get the extra 500 PQM/PQS for the extra flying that I will have to do or take the nonstop to ORD.

When I bought the ticket this was the only option given by my company travel website or it would have been US flights.

So how much grief will I get from UA to stand by on the earlier flight to SFO and then take 286 or take 286 to SFO and then take a different one to ORD or take the morning nonstop SAN-ORD?

it isn't clear what you want from what you describe, but I'm guessing you are trying to separate the legs of the "direct" flight to get the extra miles, or if not possible, take the nonstop.

Not sure if the first is possible (at least not in advance), and the second will have to wait until day of departure, unless you're willing to pay.

Should be a simple SDC to take an earlier flight SAN-SFO as long as the connection time in SFO does not exceed scheduled 4 hours.

Chances are you won't be able to do the 500 miles - if its the same flight number, you'll be credited with direct SAN-ORD miles.

For the second, check at check in (use OLCI...or at points thereafter), and as a gold, you can do a same day change for free, assuming that the fare class you're booked in is open. You can either change to an earlier SAN-SFO flight, or they should, again, if its available in your fare class, offer you a nonstop option.

Note that the options offered will be within 24 hours at the time you are looking, so if theres a nonstop departing an hour after your original flight that you are looking at, you won't be able to see that until T-24 for that flight.

Verified with a GA that if I did stand by on earlier flight, I could continue on the 2nd part of the leg and would get credit for two segments.

Instead I did SDC and was able to get SAN-IAD-RIC and so that worked out better.