findark: That is VERY helpful! Yet I wonder if you're assuming "normal market conditions" and Bologna in late Sept. sounds like it's more expensive than normal. You said $8K isn't a fair comparison, but $33K is the actual price for 4 tickets in J class for the same United flights that have the mileage upgrade award option. I'm not finding any "good fares" to Bologna for under $1000 per person (and it's closer to $1400 per person if I don't want to do an 8+ hour layover (there's a sub-$1,000 ticket if you have a 31 hour layover!). So it's a very expensive run.

Perhaps waiting longer to purchase our tickets would result in an airline fare sale or even being willing to fly somewhere else and take the train in. However, we only have 10 days so I want to get to Bologna and not spend an over-night in London/Munich/Frankfurt or take a 3 hour train ride to get to BLQ.

Other J class tickets on British Air, Air France, etc. are also far more than $2000 each. The cheapest price I could find is $4K on Virgin Atlantic/British Air ($16K total) for a 21 hour layover on the way back and a 6 hour layover on the way there at LHR (which I do NOT want to do).

The next most reasonable J class ticket is about $5K each person. Rather than pay $20K cash (!!!), I'm thinking it still makes sense to pay $10K cash and 160K miles with the *hope* of being upgraded to J. If we're not upgraded, they'll refund the $550/person per inbound/outbound flights ($4400 if I'm doing my math right). So then I'm paying $5600 for economy round-trip seats to BLQ on United. Not ideal since United isn't known for their service, comfort, or food, but this is pretty equivalent to the cheapest economy ticket on other airlines with short layovers (meaning under 6 hours) to BLQ. A Google Flight search shows it is $1400 round-trip ($5600).

Does it make better sense now? Or am I still making a wrong assumption somewhere?