I don't mind 5+ year timeline granted I have a thought-out plan ahead of me, or even moving temporarily per se.. however, it must be considered that will reduce the household income and cash that can be used to invest in real estate.

You have seen how a deterrent made things temporarily better.

If you want to stay married the only people that should be in a guest room is your own kids or family visiting "temporarily"  Its a road that will ruin a friendship and/or a marriage.  

The parking arrangement through the Exchange Accommodation Titleholder gives you the opportunity to temporarily "park" the property while you make your intended capital improvements so that it will all qualify as real estate.

The problem with older properties in general is the insulation in the walls has deteriorated from it's original noise level dampening and the floor structure has weakened with age.

As mentioned, that's what renter's insurance is for.But, if it was me, I'd give them a choice of a rent reduction for each day until the unit is fixed, or for you to get them a portable A/C unit, or put in a window unit temporarily (and they can choose which room it goes in), that they can use until the work's done.Then, keep the A/C unit for future emergencies.We had a couple spare window A/C units for these situations.Legally, you could just tell them that's what renter's insurance is for.  

You weaken your rights to be indemnified by acts of the PM making them an additional insured, that's their purpose.

Can you put a window AC in temporarily while the part comes?

You also evict him while all that is happening for him so he now has no place to live temporarily.  

This is becoming more common.As a manager who has had to get a tenant to move out temporarily because of a flooded pipe, etc., I can tell you that even in a very simply-worded contract, with a section that clearly and simply explains that if something happens, the landlord is not liable for damage to their property, etc., and that we strongly suggest they get renter's insurance to cover them, tenants will look at you in shock and amazement that they have to pay for their hotel bill, beyond the reimbursement for just the rent amount (which of course doesn't touch the hotel bill).