Congratulations Heath on your growing family.
I can comment on the two cars that are in your price range, being the proud owner of both a family and a fleet. The former consisting of a wife and three children, the latter of a 300Tdi Defender Wagon and an '03 TD5 D2A auto.
The D2 is a recent purchase, and replaces a RRC manual. My wife drives both the D2 and the Defender equally well, but prefers to drive the D2. However for long trips the Defender is the vehicle of choice, partly because it's better kitted out but mainly because it's more trusted.
The D2 has computer related idiosyncracies. For example, if you turn the foglights on and then turn the ignition off, when you turn it on again, you'll have to reactivate the fog light switch (it's not an on/off switch, it's a signal switch). However if you turn the wipers off with the rear wipers activated, then when you start your wipers again, the rear ones start too, and require an ignition off to reset. The Mexicans (3 amigos) pop over for an occasional visit too, and there's oil in the loom (new one on order). Then there's technical stupidity, like putting the DVD player under the drivers seat.
We're contemplating a Melb - Perth trip, and if we didn't need a 7 seater when we got there, the D2 wouldn't even be in contention, the Defender would be doing the trip. But we need the 7 seats and the D2 is a lease car, so the extra mileage helps it. It's kind of disappointing to have to take the D2 over the Defender.
Both cars are really good offroad, both are a pleasure to drive. All cars have issues, and with both of these cars you can be sure that the issues are not significant (3 amigos, oil in loom...) and that they're relatively easy & cheap fixes. I bought a Hawkeye the week I bought the D2, I'm still learning how to use it (there's no manual about what you can do with it), but it helps to direct your efforts - for example, the Mexicans are prompted by a shuttle valve problem, so I know I don't have to go check wheel sensors etc.
My choice is the Defender, but the D2 is not as complicated as I had feared. The D2 will be easier for loading a pram in and out of for your wife, and will have all the child anchorage points, as well as a middle lap-sash belt. The Defender will be easier to customise and easier to live out of in the bush.
As for the series Landy, I had one as a daily driver for 20 years. It had done the Simpson (East - West), gone Melbourne to Darwin, as well as Melb to the Kimberley a few times. But the Defender is just soooo much better - Economy, Braking, Reliability, Air Conditioning, Suspension.... The series would be a nice project to own, but the Defender will better support your family.
