I work with an agent with a private membership club model which costs about $15K per year. I will sometimes use miles for premium air, but buy it other times. It really comes down to when there is value in the redemption vs purchase. I tend to take trips with a lot of moving parts as well and sorting the right meet and greets (gate), guides, activities, movements, reservations etc can be a bit cumbersome. It sounds like you are looking for bespoke/full service. Fischer Travel does this, but it's a large team and you're not directly dealing Stacy or Bill a lot of the time. Their entry is actually a fair bit higher at $100K. Other groups advertise being more for the young and hip, but really comes down to needs. If you spending $250K/year on travel I would suggest moving in.