If the landlord were to go to court and win, the landlord still loses.This is all about making a reasonable accommodation. 

You do have to pay something to enrol as well as books... but you save on accommodations and transport. 

That is a recipe for disaster.This is unchartered territory for the most part, so you have to ask yourself whether you are willing to push the limits and potentially go to court to help set some rules, or work within the framework to find the most qualified tenant.Here is a good form to require for the next step:FORM TO REQUEST AN ASSISTANCE ANIMALWe are committed to granting reasonable accommodations when necessary to afford persons with disabilities the equal opportunity to use and enjoy our rental properties.Under the Fair Housing Act, a person with a disability is defined as a person who has a physical or mental impairment that substantially limits one or more major life activities.

It's nice to try and accommodate them but nobody promised a life without problems.

Enough accommodation for existing demand, whatever it may be?

The law requires you to make a "reasonable" accommodation.

I want them to do well and be successful, but recognize that it is a slippery slope to allow for accommodations and flexibility in the lease policy.

After 10 years of this, management may be ready for easier things also- and then you need to accommodate them, or bring someone else up who can handle the tenant-tenant interactions. 

Airbnb, VRBO/HomeAway, TripAdvisor will all have people searching for mid-term accommodation.

You will charge guests 13.42% tax (excise and transient accommodations) which you will collect and pay the state quarterly.