I'm really glad you're considering this, I'm currently stuck trying to get the drill so I guess I'll come back later once the tip system has been improved.Yes you are right on this one. We were under the impression the tip-system will actually make things too easy but it seems it is even lacking a bit. We will modify the tips to be more straight-forward like you explained where the location and item is more straight-forward.
The submenu was in the original plan actually and it got scrapped since our aim is to eventually add mini-scenes through-out the maps (like finding characters doing sexy things that are not plot-related) in various rooms on your way to the destination.
The locations feel "empty" now which results in the "5-clicks to go" but in the future it will work out (we hope) in a more rich environment. One example is Alice getting a tan where she doesn't affect the plot but it is nice to see her there.
On the second item, it's not really about emptiness, it's about how to navigate the houses. You or the artist may have the layout clear enough in your heads, but from the player perspective (at least mine) it's hard to get (for example) from the front of a house to the back, since I don't know which in between places I need to go before (front->living->kitchen->backyard).