The stucco on house is old and in bad shape so probably needs to be removed or vinyl side over it.Question: If I decide to an an offer how much should I budget for repairing this and how complicated and expensive will this repair be.

I'd like to self-manage the first rental as a learning experience but would eventually plan to transition to a management company, so the numbers have to make sense to cover this expense.  

The $840 mortgage and expenses are covered nicely by $750 in rent (housemate on my primary residence) and $1550 in gross rent on the duplex. 

Issue is Electric vs gas :(  utils will be expensive and you need to address that at lease orally with the prospect.

I think I have the swing of the expenses finally, but I am confused about the amount I've invested.

I can refer you to my investing group's financial experts (accounting firm / law practice), if you like.Where the issue may be getting confused is that the interest on financing is an operating expense for income property, but the principal portion is booked under debt service, as I understand it.

Even if all expenses and debt service cost 60%, you'd still have a 10% Cash on Cash return.

The contractor on Property #2 was more expensive but nearly turnkey. 

Calculate your NOI and then take out capital expenses and debt service fee to calculate your cash on cash return.

I really like doing land contracts because you don't have the expenses that you have with a rental.