Transportation certainly was an afterthought for most resorts. But, they've done a lot to improve the bus system in the past 5 - 6 years, imho...mostly station upgrades, but they do seem to be taking it more into account. I really like the bendy busses too. Very comfortable rides, and that extra capacity is lovely.
And, tackling the snarl that was DTD was a fantastic spend, imho.
I would love to see an expanded transit system, but it's just not practical, financially or even physically in some respects.
And, if I was to choose one, the current monorail designs are not something, as an operator, I'd want to maintain, much less expand. The largest issues being the fact they are Imagineer designed busses on square concrete that look cool (even though Gurr is my favorite imagineer)...vs something designed more as a mass transit system, to include forethought into what happens when things go wrong.
The difference between designing a dark ride omnimover, or a "toy train" setup for a theme park (which, again, all respect to Gurr, is what he was good at, REALLY good at, but even he'll admit he was more of a seat of the pants tinkerer till it worked sort...who liked to learn from mistakes) is a slightly different set of skills and talents than what is required to plan a reliable transportation system with appropriate failsafes/failovers/evaculation plans.
Staying on the ground in the first place is a nice start...