On the one hand, Woz should have known better.
On the other hand, you can go coast-to-coast using nothing but Interstate highways, which have standardized lane markings, standardized signage, limited vehicle access (no side streets, driveways, or parking lots, only onramps, offramps, and vehicles on the shoulder), no pedestrian access, and even limits on grade and curve tightness. Given the limited scope (compared to being able to drive on any arbitrary road with sometimes non-standard signage), I could see thinking they could have had something ready.
I have to agree with Woz -- Jobs was a showman, but everything he'd demo and talk up was actually a working product that was ready to ship; Tesla is a showman, but likes to talk about what he assumes is possible.
I have learned to ONLY buy a product based on what it can do now, not on any promises of what it will do in the future; sometimes those future promises actually come through; sometimes those future promises are strictly vaporware based on the marketing dept. just claiming stuff without asking the engineers; sometimes, the company are jerks and just decide they're going to drop support rather than add promised features; sometimes, the programmers/engineers find the features are difficult to impossible to add.
I recall a storage array a few years back where they promised it would support deduplication with a future update. The thing had very low RAM, like 128MB or something, and they could not get everything to fit but figured they'd find some "fat to trim" and get it all to fit. After about 6 months they admitted the system simply didn't have enough RAM to support the additional features and it was not going to get them.