If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

Covering most of the routine maintenance items here. 

Focus on the simple basic transactions like a dentist does with routine teeth cleaning.For all agents out there, I'm not saying there isn't a need for high end service because top agents will always be need and wanted by their clients for no other reasons than perhaps the security that comes from the feeling of paying top prices for top service. 

That's actually a comedy routine to an experience investor.

While you can't create limitations against their lease and legal rights they have for quiet enjoyment, things like keeping common areas free of clutter or routine maintenance items that are tenant responsibility can often be added to help keep the expectations on both parties clear.

This needs to be highlighted in the lease and acknowledged by them.Security Deposits: You can’t use their security deposit for routine cleaning, but if they leave things in bad shape beyond normal wear and tear, it’s fair game to deduct cleaning costs.I’d start by having a straightforward talk with them about the importance of keeping things clean for health reasons and property preservation.

Spoiler alert: These are a routine occurrence with emotional 18-22 year olds.Thats no Joke... 

As for the way that they are living, you should be doing routine inspections and then hold them accountable.

Not 2-hour morning routines or more education/inspiration/motivation/etc.

To determine if the expense should be classified as a capital improvement or a deductible repair, the context of the expense is very important.An example is, if an item of expenditure is part of a general plan of modernization, renovation or rehabilitation to equipment or other business property, it typically must be capitalized even though on its own it would be currently deductible.According to IRS Code, expenses that you must capitalize are those that:Materially increase valueSubstantially prolong useful life (including replacement of deteriorating assets)Adapt the property to a new or different useHowever, you are allowed to deduct expenses and fees for routine maintenance and repairs that help keep the property in efficient operating condition.