No it doesn't hurt to ask but the calendar is up to date 99% of the time.
You say it sleeps four but I only see one bedroom: Yes, it is a small apartment and is best suited for parties of two. But there is a full sized futon in the living room that can be used as another bed.
Maximum of 4 persons & 2 pets: No exceptions.
Is the apartment on the water or is there a view of the water: No, the water is a little over 1/2 mile straight down the street. It's a nice walk or bike ride.
How close is the park: The apartment is situated 1.3 miles from the park.
Will we meet you: Since we live on the property also I like to to say hi, introduce myself and answer any questions but that would be up to you.
What other fees are there: We do not charge the standard 8-15% additional booking fee that you are accustomed to paying elsewhere. The rates are outlined in full on the reservation and payment page.
When will I get my security deposit back: Assuming everything is in order after you leave, most people get their security deposit back within the first 3 days but I am human so if you haven't recieved it in a week email me.
Is the apartment available during the winter: Maybe into the first week or so in January.
When will you put the new calendar up: Usually November or December but we are always taking reservations so just ask and you may get in before a price increase.