Question for the experts: is there any reason to not accept prepaid utilities and monthly pet fee?

Rough numbers are as here: Purchase price : $155k, Interest rate: 6%, Down : 25%, Closing Cost: about 7k (including 2k of prepaid and escrow), also Closing costs can't be rolled into the loan.

Plus, they understand that $ in the bank in pre-paid rentals is better than a signed lease.

I had a PM get all excited (me too) about 9 months of prepaid rent. 

The few that fight it in court will swear the rent was prepaid for 2 years.  

I do have a great credit score and debit-income ratio.

That said, in my experience, most  folks who are seasoned contractors don’t ask for prepaid payment in full.

I think Western Union or maybe Walmart Money Services should be able to do up to a certain amount with a debit card.

And section 5-02-080(e) of the Chicago Residential Landlord Tenant Ordinance (also known as the RLTO), states that "...the successor landlord of such property shall be liable to that tenant for any security deposit, including statutory interest, or prepaid rent which the tenant has paid to the transferor."  

If you pay a contractor with a debit or credit card, there is no need to issue a 1099-MISC for their work.