My experience?

Flat roof = leaks

Extra penetrations and walking on a flat roof = more leaks sooner

I'm probably less tolerant of leaking roofs than most people.

I'd build an observation tower instead. perhaps with a dumbwaiter installed to haul the cooler up and down.

Was there any money given with that idea to cover the cost of construction and repairs?

Mark, no money has been exchanged as yet. Husband has several roofers coming out to bid the job. We're hesitant; as Rwiegand mentioned above, concern for penetration.

The best roof top terrace has a roof over it and windows all around it.

Widow's walks were not uncommon on 19th Century homes overlooking the Long Island Sound where I used to live. Below is a modern mansion--9,000 sf. $24 million-- in the Hamptons overlooking the Ocean incorporating the design. (Though I'd bet they are non-functional.)

Photo: Kerrigan Country Realty
However, roof terraces are common indeed in the ritzier renovated sections of downtown Toronto where yards are uncommon and original flat roofs abound. The last time I put one on an old home, turned into a five-plex, we took some efforts to make sure it could be removed relatively easily to access needed roof repairs.

Is it worth the extra expense? In the eye of the beholder.

Worthy where on Lawn Guylind did you used to live? I still live on Lawn Guylind part of the year. :) (Dare I admit I grew up in Great Neck?)

Afraid we were poor plebes from the barrier island south of Long Island--Long Beach, where my maternal grandparents lived in one of the still standing original homes. (There's a plaque at the front steps confirming the home's status.)

315 Penn St. W., Long Beach, N.Y.

Note the nearly Century-old roof terraces 100 meters from the Atlantic Ocean.

My earliest memories are of sun and sand and seaweed steps from the front door.

Which, as my sister documented a few years ago, can be in the front door.

Long Beach Boardwalk, re-arrangement courtesy of Storm Sandy

Later I lived in Plainview, Brentwood, Glen Cove, Greenvale and Upper Brookville. Peripatetic.(But my range is limited!)

I LOVE the look of a flat roof, but that was a sticking point with hubby. So we compromised and have a single slope with a parapet and 'straight' sides that hide the shop and it's only visible from the rear of the house. I just couldn't do the flat roof and say I wanted something low maintenance... so - while a rooftop deck would be awesome... I would be concerned about execution unless you have really low average annual rainfall...

Rooftop terraces are very common on newer townhouses and duplexes in the area I live (South Florida/Miami). We are in the process of creating plans for a new townhouse and are definitely going to have a rooftop terrace. Because the lot sizes are relatively compact, a roof terrace provides an outdoor space for entertaining and privacy that the small lots usually don't allow for. We have been living in a townhouse with a 3rd floor terrace for the past 5 years and haven't experienced any leaks at all. I am attaching a few photos of what we hope our 3rd floor terrace is going to look like once we are done. Probably not THIS extravagant, but it's help to have a vision!

Steam MIA, that is GORGEOUS! We are moving forward with our rooftop terrace. We found an Austin company to do the install at a reasonable cost, $2,000 + railing expense. However, I wish I had Southern Florida views to go with it.

Amygillis, well these are in Doral (suburb of Miami) and are quite a ways from where we are building but they are good to use as a reference. If I showed another view you might be able to see Mt. Trashmore in the background and the huge utility lines that are all around! We have been going there quite a bit to get design ideas as they are building a whole complex of 3- and 4-story modern townhomes, just not in the area that we want to be. This gives you a good idea of what a rooftop terrace could look like though if you invested the $$$ in it as a living space.

Be very afraid of someone who would only charge $2000. That doesn't begin to cover the proper materials to do this correctly. Unless there is a 0 missing

Fiberglass fiberglass fiberglass for all your roof decking needs. they use it all over the island i live on.

7 years later I am sure the OP may even have done something different.

What was never pointed out in the original thread is that a low-sloped roof doesn't leak any more than steep-sloped roof because it is easy to inspect and repair .... UNLESS YOU BUILD A DECK ON TOP OF IT.

^agreed. I love the looks of those pedestal paver systems on commercial roof decks, but oh what a nightmare if you ever had to chase a problem.

Best to have the roof material be the deck surface. I am wobbling a bit from a vinyl membrane to a fiberglass roof/deck in my case. I think the printed designs are going to win out. This is a 60 MIL that is the front runner for now.

Worthy, I knew your grandparent's house from when I lived there in the 80's.