I account for $200/month of my income being set aside for routine maintenance, but I'd love to not put half of that towards grass cutting.Account Closed great advice.  

Once we are in agreement of what needs to be done (and often with me explaining why it should be), if it is mostly small, routine, turnover items, we will just have it done based on a verbal estimate.

If you decide to allow them I would step up / enforce your routine inspections to watch for damage. 

In Wisconsin: race, color, national origin, religion, sex (including pregnancy, childbirth, and related medical conditions), disability: physical or mental, age (40 and older), genetic information, marital status, sexual orientation (includes having a history of or being identified with a preference), arrest or conviction record, military service, off-duty use of lawful product. --- Milwaukee also adds on top of that: source of Income.)

I use holidays as a way to get in routinely without seeming nosy.

Often the percentage will lower if you have multiple properties, so ask them if that's the case if you are thinking of doing more investing in this area- Maintenance costs | ask for an hourly rate for general maintenance, any routine maintenance that you should be aware of, and if they have an in-house maintenance team or if they use third party maintenance.

The current tenant happens to be elderly, on disability and has had a recent surgery.

OR the 'I am or my child is now disabled and am approved for a vicious dog as my support animal. 

For example, people who receive disability payments are only allowed to receive X dollars a month and anything beyond that makes them ineligible to continue receiving benefits2.

He is disabled and I believe was only paying 300$ for rent now we have the property and his lease is expired we don’t know the exact condition of the property but we want to renovate and flip it.