So as long as it can provide insurance and pay the bills, I don't care much what it is.

I would advise you to look for a house instead of a condo.Condos have many fees, rules and can have expensive assessments for repairs and improvements that you will be forced to pay.Also Condos are a dime a dozen so the competition is fierce which drives the nightly rental rate way down.

Can I even break even if Summer rental season is a max of five months, and more likely three?  

i'm not familiar with the calculator but is your insurance assumption only $100 per month?

There is no running water, the plumbing would need to be redone. 

However, this is the first property I plan to manage myself. 

  $1250 "listing fee" to take photos and list a property is certainly not much of a value proposition if that's what's being charged. 

What started out as an opportunity to help an experienced investor find parking deals has morphed into a full blown obsession for me.

I ended up getting lucky and finding this one on zillow.The biggest problem I'm seeing is that everyone in my area wants close to retail price for fixer uppers - and people are paying it.

he is off and running this is the value of  a True capital partner..