She came back to me and asked if I would pay her 50% of my cleaning fee if guests cancel within 48 hours.

I charged fees for other violations as well but the fees aren't enforceable here in Wisconsin because the lease did not explicitly state what they would be in advance.

I had to have an awkward conversation with my favorite realtor when their broker suggested everyone had to pay a $700 “document fee” on every sale.

The Board already spends funds on things owners disagree on, such as expensive vendor contracts where a Board member gets a referral fee or is part of the contract.

I am looking into a company right now that does rent guarantee insurance and also does in lieu of deposit will issue a bond that the tenant basically gets charged a monthly fee for.

For example, an algorithm can't compare a property that charges a flat fee for utilities vs one that charges based on use. 

Because it is an investment property, you would pay all fees, including appraisal.

One of the side benefits is that I can avoid the whole draw/inspection process (not overall inspection, just the ones tied to the draws) and don't have to worry about draw fees.

Or just pay your sister a finders fee for getting the deal?

And, yes, there are years of data points to validate that just within my office, tens of thousands of dollars of wasted appraisal and inspection fees for deals (mostly not mine, thankfully) that had 0.00% of going anywhere but the "Loan Application Declined" bin.