Or would "fair" be me adding a little into the kitty?

All that glitters is not gold....is what I would tell my 21 year old self.  

Kitty litter boxes need to be regularly used and emptied.

Most of these guru programs get you in the door, provide you with some glitter and a few nuggets, then try to sell you the next level where you'll get the secret sauce that flips the coin.They're all the same.

We have one short-term rental in Kitty Hawk.Happy to connect or discuss.Mike

I would definitely focus on homes on the oceanside of Rt 158 - if you are looking in Kitty Hawk, Kill Devil Hills or Nags Head. 

You will have a better chance of hitting the 60% mark if the properties are closer to the ocean or sound.We have a rental in Kitty Hawk (what I would consider North OBX...anything from Nags Head and above).Mike

I would rather have cashflow on each place than fish for equity, although I am positive these two will have it almost immediately.As far as expenses, outside of the few thousand I want to put into the places prior to renting them, the monthly expenses would be about the same for both places.Mortgage is $675 (including property taxes and insurance)Water, Sewer, and Garbage $115 (figured on the high side) I'm assuming most owners pay this on behalf of the tenants.Gas & Electric to be paid by tentant (average is $150/mo)Total Monthly expenses = $790I'm not sure how much to put into a monthly kitty for maintenance.

Oh no, we never pour the kitty litter down the toilet (as the three unauthorized cats are standing in the doorway looking at you). 

In addition, depending on how many owners there are, the general ownership might be more than willing to each throw some money in the kitty to deal with an owner they perceive as trying to get around the HOA bylaws