With our town and maybe yours, any major alterations (work over 50% of the property) will require updating sewage and plumbing to the main line <- this is quite expensive and luckily we didn’t need to do this.

You may turn someone down in the future for criminal record and then have a life altering lawsuit on your hands. 

Also the lockbox so the downstairs tenant cannot alter the temp for the upper unit.

Not sure if that’s the reason in your area but one reason people don’t like investors is the rapid gentrification of an area which alters the local culture and makes it unaffordable for the folks who grew up there/lived there for generations to stay.

I find it hard to believe any insurance carrier worth their salt would not alter the premium based on an increased element of risk.I personally would have the seller deliver the unit vacant. 

Sounds like everyone has had a few bad experiences and either moved on or altered their lease to ensure it doesn't happen again.I'm going to stick with dogs and cats to not limit my pool of applicants. 

Due diligence should not be altered for the convenience of the tenant.Good on you for finding a cash flowing rental property

A housing provider should do everything s/he can to assist, but s/he is not required to make changes that would fundamentally alter the program or create an undue financial and administrative burden.

The problem with gifts, as I see it, is that it alters the relationship from professional to personal.

Are you willing to help him alter his lifestyle to make better use of the money he has (very low probability of success) or teach him how increase his income (also very low probability of success)?