Switchbacks and Sidetracks - Ideas for a family-oriented Railroad Game

Too bad you dropped the modular board. When I first started reading the thread I was thinking about Zug all the time. It's like Carcassonne with trains (actually lighter!). Check it here: http://www.boardgamegeek.com/boardgame/64426/zug

As far as roll-and-move, the thing is you don't have actually much of a choice, because tracks do not divide every 3 spaces. So, what is that you are proposing? Make a single choice at the end of every loop? I imagine the choice been: do I take the 10-turns loop for 10 points or do I take the 20-turns loop for 20 points? (I miss the 3-eyed BGG emoticon)

If you are commited to it, my suggestion would be to add layers of players advancements. For example, you make $100 a loop in "local" level and you need to get some upgrades to qualify for the "suburban" level, where you make $300 a loop, and then "international" for $1000 loops (set in Europe, of course). This is much like the 1967 game of the year:

Retrace (Status) check on http://www.boardgamegeek.com/boardgame/4479/ratrace

That was as far as roll-and-move went.

Keep thinking!

PS get back to modular board!

Your gameboard had improved. As far as the random events "out on the road", it depends on what sort of game your trying to make. Random events can be fine if that's what you want but its not exactly random if events only occur when you land on or pass a certain space. For example, my train has a chance to derail everytime I pass this switchback spot. This seems like "chance" or community chest in Monopoly. I may advance to boardwalk or go to jail. Personally not an appealing mechanic. What if you had swithcback spaces on alternate (longer) routes to the stations which would allow you to draw an extra card to your hand. So the player has a choice to take a shorter route to get points quickly or take a slightly longer route to gain a card that may help them in the long run. I suggest the "on the road" events be directed by the players (a player plays a derail on another player) rather than flip a card and see what happens. However, if you really like random events you could do that easily. You could have random event cards in the switchback deck that get resolved when drawn while other cards are drawn to the hand to be used later. OR you could have a separate random event deck with a different mechanic for triggering it. say a die roll after each round (or turn) or set up the random event cards to only effect certain areas of track and draw one after each round. For example, "avalanche: any train in the tunnel is derailed" or "Track Repairs: any train between northbury and union station loses their next turn". I would still prefer the players to play these cards on each other but I like cutthroat games :).
The lock and key cards would work fine. I wouldn't have the players keep them though. I image a switchback deck with (amongst others) switch cards that change the track direction, lock cards that prevent them from being switched, and key cards that cancel the lock allowing the track to be switched again. The cards would be discarded after use.
It sounds like you would like a modular board but the balancing of the points and distances won't balance, then I suggest a different approach. Put grand central station in the center of the board and add modular tracks emanating from it in each direction. Different tracks and stations(each with a designated color) are laid out. Instead of picking up blue chips from northbury and delivering them to union station for five points, have red, yellow and gray(or whatever color) at the northbury station. If you pick up red chips they need to be delivered to the red station (carville) for one point each. At the end of the game you could give bonuses to the player who delivered the most of each color. Or you could have delivery objectives at the beginning of the game for a certain number of passengers in certain colors for bonus points (sort of like ticket to ride objectives but with passengers instead of routes). Train upgrades may cost a combination of colored chips to purchase. Each station could have a set number of different colored passengers OR you could have a mechanism where new passengers "spawn" at each station throughout the game.
Anyway these are just a few suggestions, hope it helps

How about adding different goods transports to the passenger options?