I have personally known 2 estates in the UK that were built in the 1980s and 1990s that were "creative" in the extreme - and a fucking nightmare to find anywhere on them.
One of them has achieved wider notoriety, although maybe not any more - the Peachcroft estate in Abingdon. Absolute disaster zone, especially if you went in the Wrong Entrance (there were 2, not sure about now) and this was before mobile phones and sat nav etc. It's probably ok now.
The other one was near my parents and was of similar ilk, but with more "Walks". Little blocks of 3 or 4 houses, set at angles to the next little block, on curly roads, with no direct parking access etc. that you had to walk to, as described. Definite "calculator in the ceiling fan" effort, that one.
I don't know WHO thought these things were a good plan - the architect/planners apparently thought it would be more "interesting" for the people living there 

than having them all in straight lines with sequential numbers.
Hopefully they've learnt by now? but it doesn't sound like it. :(
My own road in the UK had its issues - I was no. 1 but before me there was a 1A and a Hall. 1A was particularly hard to find, so I'd often get the door knocked after 10pm with Pizza Delivery Guy looking for 1A, and I'd have to pretty much walk him to where it was. You could always tell when it was a new PDG, because he'd knock my door again...
We had a very irritating issue when we moved to Australia - kept getting post for Not Us, Lot X, Our Road - when our address was Us, X Our Road. Turned out that a new build quite a way down the road had been parcelled off as Lot X, but the post office hadn't twigged, and quite often companies left off the "Lot" so it would just be numbered X Our Road.
And then there is the issue of us being on Our Road, Our Town, Postcode - when there is another Our Road in Next Town, same Postcode (because Aussie postcodes are considerably less specific than UK ones - they cover whole towns/suburbs). Next Town is the same name as Our Town, just with Park after it (so Our Town Park)
And then if THAT wasn't all bad enough, there is no front access to our house, because it's on a busy main road and there is a named service lane behind us, which we use to get to our house. So our directions are always to use the named service lane behind us - which can still cause issues because our address is still main road, not service lane. Sat navs/ Google maps try to send you to the main road side of our address