In the reimbursements example, the goal shifted, by design. The environment moved from high-trust to low-trust as the department grew, and the aim moved from "keeping people happy" to "spending less money"/"not being taken advantage of". Not defending it -- I hate paperwork like this -- but it seems almost inevitable as groups of any kind grow large enough and you actually can't assume good faith anymore.
So things like reimbursements are handled by a university trying to implement a state government's interpretation of both granting agencies desires and federal and state laws/regulations.
My university seems to be going crazy with rules lately. My hypothesis is that the state, and by extension the university, wants to button down everything so as not draw attention of the federal government (given who is in charge). It's taking already stressed professors (funding cuts, etc) and piling on more stress.
I would do the typical thing of "take picture of receipt, upload receipt, specify how much it cost, etc.", and for the most part it was seemless and it would be sent to my bank account.
One time, I bought a box of Fiber One bars at a CVS Pharmacy and expensed that. I got a phone call from the billing department asking why I would expense something like that and I said something like "because I don't usually eat that healthy during business travel and I suspect you can guess the reason after that". They told me they would get back to me, and then I got an email telling me that they rejected the expense report and I would have to file it again to get the rest of my stuff reimbursed.
I can be a pretty petty dude, so I filed it again, completely unchanged, I get another phone call telling me to remove it, and this repeated two more times. Eventually I complained to my manager and he was able to get them to let me expense it and it all worked out.
I find it amusing, because the box of Fiber One bars was less than five bucks. I suspect all the time that they wasted of theirs and mine probably cost considerably more than the $5 would have saved from not covering it.
To avoid people just forming a personal company and declaring everything they spend a business expense and thus not taxed there are rules around what can be counted as a business expense.
If you instead want to take your salary in the form of Fiber One bars, but pay taxes on that spending in dollars, then your accounting department might have had fewer issues.
Usually, if your per day expense is less or equal to the guidance (where I work we do $90/day), no one cares. If you go above, you pay. The per day expense is for food. Alcohol cannot be claimed as an expense unless you are in sales.
Similar for me in the corporate world, in the 80s, I just had to save the receipts and give the to the Department Admin. Easy as pie.
Then that all changed in the 90s. Everytime I traveled, using the 'canned' system provided to us, you could spend days trying to fill in the forms. It would ask you for all kind of codes no one knew to supply.
Multiply that by 10s of employees, there is no way firing a Dept admin and contracting that out saved any money. It has to cost the company 2x or 3x as much as one admin costs. And that is a low-ball estimate.
Sometimes it's hard to see the incentives, but once you do - it all makes sense. And often they're contrary to what you would assume would be the company's goal.