Any chance you could manage with just carry-on luggage? A whole lot of transit problems go away. And the lost-luggage odds go to zero.

You could plan on buying some souvenir clothes at your destination.

I often wear clothes on the flight that have just reached their end of usefulness. Toss them at destination, thereby making room for new purchases. I did have to give up taking the socks with big holes in them after a trip to Thailand where it was always necessary to remove shoes for temple visits.