What I would be concerned with is if you can lower your cost of living.

My concern here is that people can get pissed off and potentially damage the property when they are forced to move out. 2- a more passive approach to just suck it up and when its time to renew the lease then increase the rent by several hundreds of dollars so that they will leave on their own.

It's unusual to have be questioned by an underwriter about why he financed a loan with a private lender with a poor reputation, however, if it's a concern that he'll continue to be asked about it, I recommend creating a letter of explanation that clearly explains the situation.

The other comments on this thread may be correct for their part of the country, but in Chicago, you need to abide by the RLTO which states  "(h) "Rental agreement" means all written or oral agreements embodying the terms and conditions concerning the use and occupancy of a dwelling unit by a tenant." 

I fully plan on 1031-ing every property I ever own as a rental, so I'm not concerned regarding depreciation recapture.

But, if you're at 5 months already and they want 6, then that shouldn't be a concern (it's usually 60-90 days for credit / background reports and 90-120 days for appraisals). 

I, like John, would be more concerned about the dangers of having a weirdo show up.

Or are you more concerned about cashflow after retirement and have no plans to leave your W2?

Such an arrangement could be modest, ranging from 1% to 5% for the seller, and would only come into effect in the future upon the sale of the property.Sellers will likely have concerns regarding the assumption of liability.

According to the Fair Housing Act and the Americans with Disabilities Act:Even if a landlord has a no pet policy in place, the law does not consider service animals as pets and therefore the service animal is exempt from such a restriction.Service animals are allowed anywhere a person would go, including food areas that would normally restrict an animal’s presence.Landlords cannot charge a pet deposit or pet fee for service animals, however the tenant is liable for any damage that the service animal may cause.Landlords can require written verification from the tenant’s health care provider that they are disabled but cannot ask for any specifics about the disability.Landlords can require written verification from the tenant’s health care provider that the service animal is needed.Landlords can request copies of the animal’s health records to prove the animal is in good health, parasite-free and immunized/vaccinated.Landlords can write warnings or even evict a tenant with a service animal if the animal is disturbing others, posing a threat to others or causing considerable damage to the property.In other words, you can ask for appropriate paperwork concerning the tenant’s need for the service animal and to verify the animal’s health.