Max out the number of people you can get comfortably sleep there, make the property nice and unique, and get as much money as you can for those 8-10 weekends/year that really matter. 

Should I put a lot of money into high end or unique upgrades that will make my rental stand out?    

That being said, everyone has their niche and that may be worth looking into. 

Do you really want a LL you don't know, nor do you know their qualifications giving you advice on such a unique situation?  

Thanks Sorry, not in a forum post, look at the aspects I mentioned and each requiring analysis, there is no rule of thumb, golden rule, begin by understanding that every property is unique, no other property is identical on the face of the earth.

I've found my flexibility on dogs has put me in a niche in my market.

As many of us have created resources around our niche (websites, blogs, etc).

Philly landlord tenant court is certainly a unique version of small claims court. :-)  I was a mediator there during and after law school.First this is not legal advice - just my required disclaimer.  

You may benefit from a niche lender who's rates are in the 8% range rather than hard money.  

While some of these are legitimate concerns when starting a business, they should never stop you dead in your tracks.The beauty of real estate investing is that the majority of these concerns can be overcome by simply choosing a niche that fits within your level of risk tolerance.