Yes for what it is worth I have god status on a single airline (and thus their alliance). I always put in for an upgrade, however most flights are getting quite full (full because the economy is doing well, so making money, but less seats). For the last year I have flown ~50 times and have been upgraded about 2/3 of the time. I work for a startup so business is out for everyone, CEO on down. We do pay for premium economy which on international is better with more room then economy. Of the 8 flights on this trip I have one confirmed upgrade and waitlisted for the others. My guess is I will maybe receive an upgrade on half. Now that being said I have used miles for family vacations (all in business) more then once so there is that. :)

Using your miles to upgrade to business and save some sanity probably trumps using them for a family vacation where you could probably get something on discount anyways (unless you have to travel to India or Australia for family a lot).

I have a lot of miles. Over 2m at one point. Flying and affiliate credit card I use to pay for the trips. Pretty easy to knock out 10-15K a month in travel on the card, which goes direct to miles. The family trips are key as spending so much time on the road means that time is even more important. Round trip to London, round trip to Japan for 3 in business was 100K and 200K miles total for each trip (all 3 tickets) with out of pocket only like $500 and $1000 (taxes, airport fees, etc.) Key is to be flexible on time and flights and destination. I call or visit the airline office (JAL) and say, hey we want to go to London or Tokyo or Singapore or Paris between these dates, business class and are will to fly from these airports in CA. They will come back with flights on them and partners. I just pick one and go. Who cares if you have to make it from SF to LA to make the flight? It’s a cheap ticket. I cannot speak highly enough about the service level at JAL. If you have to travel for work and be away from family, it is key to maximize the return for the family. I will say traveling sucks but FaceTime and the like has made it so much better to keep in touch. I always block my schedule no matter what timezone for a call each day with my family.

Curious if you had to estimate how many days are you not in based in your home location a year?

Between 7-14 days a month for around 10 months a year. It will be less next year as I get the right people in place.