Only the Attorneys will win.

A young potential tenant (college dropout I believe in early 20s) has applied and has excellent credit score and credit check but the credit history is just a year long or so.

I agree and you make excellent points.

There are no guarantees that you will win.5. 

My property manager does an excellent job and allows me to separate myself from any personal relationships with a tenant which is something I personally think is mandatory for all landlords.Don't beat yourself up for having a good heart and since you know this about yourself, put things in place to manage your business affairs.

Your manager should want to do their job well and be dedicated to maintaining excellent standards. 

If I can make out with +$200 a month, I'd consider that a win for me.

Excellent credit score.Thanks a lot!

The potential tenants are aware that I'm the PM and neighbor.Rent: $1,600Tenant 1: a few years about of school, excellent previous landlord references, two jobs, seemed clean cut and put together, Gross Income to half / full rent: 6.77x Half Rent / 3.3x Full RentVolunteered dad (well qualified cosigner) who agreed to be cosigner and passed all screens.Tenant 2: Similar life status and feel as Tenant 1, lives with parents (no rental history), toured apartment with his mom, Gross Income to half / full rent - 3.6x Half Rent / 1.83x Full Rent.Would you require a cosigner for tenant 2 or is tenant 1's dad enough when combined with both incomes?

Would I be able to have a friend offer cash on the same property, then essentially wholesale the property to me (he makes a profit selling to me and I still get the deal, win win)?