Renting in Fountain back in '09 and running the 'Gateway' (C2 with c4/hisec static) were both the most profitable (at the time) and admin intensive things I have done in EVE.
Our relationship with our landlords was pretty tight - obviously second class citizens, but we paid up in advance and still turned a good profit + actively assisted in fleets and intel channels. The issue was keeping a ledger of all rent contributor corporations and holding annoying 'city hall' meetings regarding people thinking they should pay less and their in-alliance corporate neighbours should pay more. Essentially this turned into the pragmatic camp being forced to devise ever more elaborate ways to explain and enforce the 'how to raise the funds and profit - 101' guides we'd cobbled together while trying to shout down (and being shouted down by) a combination of embezzlers and wannabe Ayn Rand's who had some kind of insane notion that an industrial alliance should be the dominant partner in a rental relationship because 'we got's rights goddurn it' (my eyes rolled to the point that I needed the assistance of an optometrist to get back to the paper work). That's an example of management/people related paperwork and trust me, I never really want to go back to that, even in as big a supporting team as I had, if only because unless you can bring the hammer down on non-compliant groups, you'll start to get 'bright spark' ideas that basically amount to pocket lining at the expense of paying the rent.
Environment driven paperwork, of which wormholes are the only example I can think of outside organised Incursion fleets with rotating rosters, was much more palatable to my tastes. The lack of local and market facilities really helps people to come around to the concept of deferment of gratification until the right time, simple because the rewards are so great. When even your most casual and thus lowest paid site runners are making a few billion in a week in a c5 or c6, the issue of embezzling and pocket lining is killed immediately for 'low rent wannabe crims'. All your low-sophistication scams (outside emptying arrays, which comes down to mechanical security and awareness campaigns) pretty much lose their risk/reward scope or fail outright to get anything going. The downside is this leaves your truly sophisticated, goal driven or pathological agents in the mix, without competition or the potential of 'allying with a try hard who blows their cover'. This increases recruitment checks (which are limited in their ability to discover truly good sleeper agents anyway - but keep out the rabble), increasing paperwork, and it also means you need to know that several people are responsible for calculating payouts, to ensure parity and the ability to verify if someone is, through malice or incompetence, diddling the numbers.
This all sounds very arduous, but to be honest, wormhole paper work, after codifying the format of it and 'best practice' (all very boring when you do it I know), ran smoothly and because any threat to the system was credible and infrequent, people driven by a more adversarial work-ethic had someone other than their colleagues to 'worry about'. It was the constant stream of bile, bitching and try-hard scam attempts (that largely failed) in null that made the paperwork difficult - though this is coming from the POV of a young (now defunct) alliance led by a small group of very different (and abrasive at times) individuals, so it is not reflective of more dictatorial/established alliances who can trade on military power and brand to ease the pressure of discontent when dealing with financial/logistical 'discussions'.
Wall-o-text ends.
tl;dr - I preferred wormhole paperwork to null paperwork, but the rewards scale favourably compared to the complexity of the work in both cases. Reasons are in the text above. Learn to patience!
