It seems our plan (to book tonight) for 2 award tix and 1 paid

EWR-SFO-NRT on 4/24 (without research, I would love to get CA ones through Tronto)
(KMQ-)NRT-IAD-EWR on 5/9 (I would love to get NH NRT-JFK...)

I don't think domestic NH flights can be difficult to obtain due to Japanese holidays around that time, so I would buy from NH

HND-KMQ on 5/2 or 3
KMQ-NRT on 5/9

Then, I will buy one more tix for my father-in-law to visit us together back to the US. Current plan includes small trip at the end like below.

KMQ-NRT-IAD-EWR
EWR-IAD-CVG
CVG-ORD-NRT-KMQ

Qestions are;
1. I will have use multi-city search to buy tix, and is it sill okay to request upgrade with milage and co-pay?
2. I would like FIL to get C seat and I know I have better chance to get a seat... Do you have any experiences that one passes an upgraded seat to the other party member who is on the same flight?

I appreciate your help, in advance!