I went there to have the water turned back on and started getting caught up in what the preferred order of operations should be.

From, "someone ate my food" to "someone takes long showers and uses up all the hot water" and even arguements over parking spots.Who wants to handle all that extra nonsense for "free"?

Costs will be far lower, but an owner/operator would still get the benefit of staffing and material efficiencies. - You could consider owning those as rentals and leasing out to the businesses. - You could sell the land to an owner/operator who wants to build assisted living. - You could own and operate those yourself and just hire great management or bring in a management company. 

Thermostat was off the wall, laundry room filled up to 3ft with dirty clothes trash everywhere, bed frames dissasembled and no water.

Instead when the washer drained water went everyone.

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.

However I would probably bill it back to the tenant monthly if it was based on usage like water.

Or maybe use the cash they’re willing to front for a bigger better deal where the cash can get used more efficiently but again, how?

We had redone a brand new kitchen and included a new water line for a refrigerator cold water dispensing.

@JD Martin the biggest issues have been related to furnaces, hot water, a missed clean, and broken hot tub. generous refunds have ranged from 25-100%, it really just depends on variables like nightly rate, guest demeanor, impact on their stay, etc.