David,Before you choose a lender, I suggest you attend a seminar conducted by Joe Massey at Castle & Cooke Mortgage.

And make sure they understand to NEVER pour cooking oil/grease down the kitchen sink or the toilet. 

Previous owner was a heavy smoker and left behind all furniture and personal staff(that was part of the deal).

Do the tenants cook for themselves or does the operator have to supply all the meals?

I am wondering if there is an easy way in Cook County to find the amount of legal units in a multifamily property without pulling a zoning certificate.My situation:I have a property that is being marketed as a 5 unit, 3 units main & 2 units coach house.

If a tenant prepaid a year in advance and the PM passed along all the rent to you at the beginning, they'd have to bill & collect money from YOU to do necessary repairs to the unit during the year, they are not going to do that.As for the weed issue, most people I know smoke weed in some capacity these days, and I'd much rather have a weed smoker in my units than a cigarette smoker.

I don't care how well you rehab the house and if U pull all permits if your tenant base is abusing and transient your goose is cooked before you ever started.. 

I will require parent co-signers, but I think I will do other basic things - "have you been evicted, how many people will be living in the house, are there any smokers, provide references" , etc.

This apartment was occupied by smokers for 16 years.

Let me know what they have cooking next time you chat with them