Is a rail pass worth it?

Only if you are traveling between many countries in a short window. For a 3-city trip, booking point-to-point tickets 60 days in advance is almost always cheaper.

How do I handle money?

Use a debit card with no international transaction fees. Always choose 'local currency' if an ATM asks if you want the machine to convert the currency for you.

How to plan your first Europe route

Focus on three major cities maximum for a two-week trip to avoid burnout. Connect your route using high-speed rail rather than flying to save time on airport security and transit logistics.

Select your 'anchor' cities. Choose three cities that are connected by direct high-speed train lines, such as London, Paris, and Amsterdam. Don't pick cities more than 4 hours apart by train for your first trip.
Open-jaw your flights. Book a multi-city flight ticket. Fly into your first city and out of your last city. This prevents you from wasting a full day backtracking to your starting point.
Map your transit. Use the Omio or Trainline app to check travel times between cities. If a journey takes longer than 5 hours, look for a budget flight or an overnight sleeper train to save on a hotel night.
Build your daily buffer. Schedule only one major activity per day. Europe involves a lot of walking on cobblestones; plan for at least 3 hours of 'unstructured' time each afternoon to account for fatigue.

Is a rail pass worth it?: Only if you are traveling between many countries in a short window. For a 3-city trip, booking point-to-point tickets 60 days in advance is almost always cheaper.
How do I handle money?: Use a debit card with no international transaction fees. Always choose 'local currency' if an ATM asks if you want the machine to convert the currency for you.