What if one person insists on a 5-star hotel but the others can't afford it?

The person wanting the upgrade should pay for the entire accommodation cost, or the group should stay at the 'baseline' hotel and the person wanting luxury pays for their own separate room elsewhere.

Should we split restaurant bills equally even if someone ordered more?

If there is a significant income gap, always use itemized splitting. If the group is generally aligned, equal splitting is faster, but allow for 'opt-outs' if someone chooses to order significantly less.

Split Travel Costs Fairly in Mixed-Income Family Groups

Establish a base contribution for shared expenses that everyone can afford, then use a 'percentage of income' model or voluntary tiered payments for luxury items. Use an app like Splitwise from day one to track every expense in real-time so there are no surprises at the end of the trip.

Set the 'Floor' Before Booking. Define a 'Baseline Trip' that is affordable for the person with the lowest budget. This covers shared accommodation, public transit, and grocery store meals. If someone wants an upgrade, they pay the difference individually.
Create a Shared Digital Ledger. Download Splitwise or Tricount before you leave. Agree that all shared costs (taxis, group meals, Airbnb fees) are uploaded immediately. Set a 'settle up' date for the final day of the trip.
Agree on Currency and Exchange Rates. Decide if you are settling debts in the local currency or your home currency. If the latter, use the mid-market rate on the day of the transaction to avoid arguments about fluctuating exchange rates.
Implement the 'Pay Your Own Way' Rule for Discretionary Spending. Agree that individual shopping, separate excursions, or high-end cocktails are not split. If someone buys a round of drinks, they mark it as 'paid by me' in the app and assign the cost only to those who participated.

What if one person insists on a 5-star hotel but the others can't afford it?: The person wanting the upgrade should pay for the entire accommodation cost, or the group should stay at the 'baseline' hotel and the person wanting luxury pays for their own separate room elsewhere.
Should we split restaurant bills equally even if someone ordered more?: If there is a significant income gap, always use itemized splitting. If the group is generally aligned, equal splitting is faster, but allow for 'opt-outs' if someone chooses to order significantly less.