We are really wanting to purchase a "toy" like a boat to enjoy with the family and let the cash flow from the two properties pay for it. 

Due to my cheap assery, preferably like to keep our mortgage within 1/6th to 1/8th of take home pay, and set our pre-approval for about $50k less than the listed price (house flipping intentions).

When you think of hiring separate contractors for each of the big jobs -- do you prefer that idea rather than working with a general contractor who subs out those trades? 

No specific plans on what that would be, but preferable a multi-family.

But, again, that's personal preference.

As a former student myself, I’d prefer to live on the West side as well.My only concern about the West side is I feel that the student rental market is over saturated and would be worried about finding student renters each year.

Now I have contractor saying they would recommend repair of bath and kitchen and preference would be that tenant be gone. 

If the sale of the property was via a warranty deed, then a claim could be made by either you, or preferably the title insurer, against the seller.

You can also be very direct and upfront, depends on your style and how you prefer. 

He could get a preferred return for the use of capital.