Initial Placement

If possible, find a synthesis among your starting contracts. Try to find two that, say, both start in the north and go to the center or south. If this isn't possible, tend to start with the one that ends closest to the starting point of another one. Failing all else, choose the one that requires the most loads. Before deciding, have a look at the open contracts to see if there is any which would work well with the ones you hold.

Driving

When one's two rolls are "1" and "2", consider choosing the "1". If the "2" doesn't get you into a city where you need to perform a transaction, choosing the "1" could end up blocking an opponent for quite some time, which is worth a lot more than an additional point of movement. The events in the game are usually helpful, but a few of them can be quite devastating. Having to take an additional contract late in the game can be prevent you from ending play before opponents can deliver valuable contracts. Another one forces you to return to one of your contract's point of origin, which in the wrong circumstances could end up sending you to the opposite end of the board. Another forces you to visit Wien or Flensburg or München which can cost a lot of time if you do not plan to be in those areas. Therefore ... Do not go out of your way to land on event spaces unless you feel you have fallen behind. If you have two equally valid paths, one with the event and one without, you should probably avoid the event if you feel you are leading. If a move would get you within one of one of your destinations, you should land on the event since a roll of "1" cannot place a block on between you and the destination. If you are near München and need to pass through it, avoid an event since there is an event which can block that city through the end of your next turn. The same thing applies to the space between Frankfurt and Kassel.

Loading

Don't load a contract until the start of your turn. If your opponents don't know where you are headed, it's harder for them to block you effectively. But if you are going to forget to load before leaving the town, go ahead and load immediately. Sometimes loading at the end of a turn can be useful. Suppose you are in München and next need to load another contract to the west. Loading your contract that needs to go north will fool other players about where you are headed next. Another reason is that one event permit other players to move you against your will.

Choosing Contracts

Routes which lie exclusively in the north are better than those which are exclusively in the south. Distances tend to be shorter and more importantly there are more alternate routes. In the south, there are only so many passes over the Alps. If an opponent blocks traffic on the one you are using, using a detour can be very time consuming. Because the board is tall and narrow, in most games there is time to make one trip from north to south and then from south back to north, or vice versa. Try not to acquire contracts that require more than that or you may well still be trying to deliver them when play has ended. Avoid acquiring a lot more contracts than other players are holding. In the early game try not to let the number you have exceed the next highest player's by more than three. In the mid-game this number should go to two and by the end game it should not exceed one. Actually, having fewer than others would be best.

Bidding

A good rule of thumb is to make your maximum bid the same as the number of players in the game. Too often going beyond that, except perhaps when you are doing the exact route anyway and have the capacity already, is probably costing too much. Only bid on a contract if you have a reasonable chance of delivering it. Letting someone win a contract for free won't kill you. As an exception, before you have taken your first time you can probably safely bid a little on just about anything since nobody knows in which directions you're headed.