I think that's going to be tough.

Since finding deals are tough they are just staying put.I chose multifamily.

Ijust feel some of the material isnt helpful

Most likely the seller will be choosing the cheapest price which normally isn't the best job/warranty's,materials,etc.I would prefer a credit for the roof, whether that is a reduction in price or a check at settlement.

(a) Except as provided in this chapter, if there is a material noncompliance by the tenant with the rental agreement, an intentional misrepresentation of a material fact in a rental agreement or application, or a noncompliance with Section 35-9A-301 materially affecting health and safety, the landlord may deliver a written notice to terminate the lease to the tenant specifying the acts and omissions constituting the breach and that the rental agreement will terminate upon a date not less than seven business days after receipt of the notice.

Would love to do a 1031 exchange for a beach rental but seems tough to find something that the numbers work on right now.

It sounds like a tough property/project that can't be sold with traditional bank financing, so honestly the seller needs to allow enough room in the purchase price to compensate the buyer for taking the project on.

Contractors are tough to come by in Ocean City, MD when you're in a pinch.

For what you're talking about going from a ~1,000 sq ft house to almost ~1500 is a pretty material difference, as is adding that second bathroom. 

They will cause constant issues like clogs, electrical shortages, lead citations, remediation if there is asbestos in piping or building materials, etc.Maintenance and CapEx are your two most variable expenses.