yes! I used to live there. it's bonkers.
Basically all the lakefront property is not owned by people directly, but leased under highly permissive terms from a single entity (ominously named "The Lake Corporation") so they can apply restrictions about land use to owners to prohibit public access, and act collectively to try and prevent public access attempts. It's basically a Union for rich people to use to collectively bargain to keep poors away from them. totally wild.
They exert undue influence over the city's politics which is usually evident by their inherent inequity and hostility to non-members in the city.. but the county they're in (Clackamas) tends to fight them a lot. The city's officials are usually in tight with the Lake Corp (or ARE Lake Corp) so it's basically a corporation vs the county/state trying to keep poor people away.
The city's dedicated police force, unsurprisingly, are very keen on the Lake Corp... so even if you (legally) access the lake, they will send a boat out to hassle you until they find a reason to move you along - usually with the lie "you had to trespass to get here. you can leave and we'll drop it, or you can make this hard"
been a programmer for nearly 25 years now.. i understand what you mean. i find a lot of joy in not just making a program "go", but building it elegantly and efficiently. there are a lot of design guidelines and patterns that make that easier and more predictable, but i always feel there is a lot of value in trusting your sense of aesthetic and building stuff by way of discovery and refinement, sculpting.