That's a pretty cool idea. I wonder if it'll take into account things like traffic, weather, accidents, etc.

Perhaps if your Pokémon has a low intelligence stat, it'll get on the wrong bus and get lost, possibly forever. Or maybe one with a high rebellion stat will just run away. A low-dexterity Pokémon might accidentally drop their money and then have to spend time doing odd jobs to earn back train fare.

So, you'd have to plan the trip out beforehand, equipping the Pokémon with money and possibly supplies. There's a chance they might want to buy snacks, but then they could also miss their connection and have to wait for the next bus or something. They would also need money for lodging. Perhaps certain hotels would offer Pokédiscounts? Then the game could ask the real-life hotel to send a wake-up call and if they don't, the Pokémon might miss their train. Maybe Pokémon wouldn't be allowed at regular human hotels and you'd have to search for pet hotels.

Perhaps you could select the travel method. They could go by bus, hitchhike, plane, raft, etc. Each would cost a different amount of money, in addition to time. Flying-style Pokémon could just fly for free and the game would take into account windspeed and direction.

Niantic could set up one of those sites like they have for package tracking. Normally, you don't have realtime tracking, but for a couple extra Pokédollars, you can upgrade to GPS tracking and it'll show you exactly where your Pokémon is at all times.

You could also buy a Poképhone for them to call you in case of problems. They might also send you photos that they took along the way, which could be submitted by actual players and screened by a team of professionals.

Of course, you'd have to worry about enemy Pokégangs taking out your Pokémon as they travel alone. They might get mugged or kidnapped, unless you hire someone to act as a Pokébodyguard to make sure they arrive okay. These could be AI characters or even other PG players!

You could also hire snipers to take out rival Pokéshipments to prevent enemy factions from gaining power. You might hire scouts to sweep the area beforehand, each of which would have variable skills and stats.

Pokémon would then be fatigued after a long cross-country journey and need to recuperate for a short period of time, from minutes to days depending on its toughness stat.

On the other hand, they could just calculate a rough time estimate based on distance.

On the other other hand, they could just let you have the Pokémon instantly, instead of wasting players' time.