I voted for the diesel pickup and family car. I can see both being very useful to you.
The family car wouldn't be used as much, but like you said is going to need to be replaced relatively soon. I'd probably opt for the Prius as a first choice and Jetta TDI as a second choice. I've driven and worked on both and IMO its easier to get better mileage with the Prius. In the city the Prius mileage smashes the TDI, and even on the highway I seem to get better mileage than almost any TDI (that we have in the US) I've seen on these forums. Price wise they're both high now though. You can probably find a cheaper TDI, but the miles are going to be very high. As you mentioned, PHEV is possible with the Prius. IMO you/we/makerspace could help make our own 'enginer' type kit. The only item that really would need to be custom made is the dc to dc converter. One other project I've been thinking about for a long while now is a 4 door Tercel and swapping in a 1.4L turbodiesel from the European Yaris. It would be a 70mpg car easily, but I think that would be too small for a family vehicle.
The diesel pickup would be great for you for work. First getting the diesel in and later hybridizing it would be a great project and I'm sure the mileage would be very good in it.
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