I went a period here after the bubble  without ownership of property and have just closed on my 4th deal ever and my first property since after the collapse. 

Michael does design, cost breakdowns, and some project management. 

Also, I did a lot of the design and purchasing.

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I actually hired a designer from a website called People Per Hour (I have no affiliation with them).  

an interior designer can help you map out a new layout.

I would work with your agent some on making your offer contingent on a new roof (I have a sample scope of work blog post, designed for a fourplex standard shingle roof)...

In my experience, people that genuinely profit from vacation rentals are people that buy exceptionally smartly (truly unique location, and property, expertly designed for that vacation rental market in that area) and do not cut off their cashflow by using it themselves during peak times (or worse, giving it to generally unappreciative family members) and understand that regular reinvestment in new furniture, dishware, and maintenance is not optional. 

I graduated in 2012 with my ASA in Interior Design, I am not licensed but I've worked with a few designers in SF, and selectively on my own staging homes or commercial spaces.

@Shawn Connors -I hate to burst your bubble on this but I'd say your time will likely be better spent looking for another property.Range of value, from 12% Cap with 50% OER, to 8% Cap with 40% OER, is $300,000 to $540,000.