My parents and my aunt and uncle are TS owners at Harbor Landing in Vineyard Haven. They have been owners since it converted to TS in the 70's (my aunt actually sold them back then, and convinced her husband and my parents to buy in.)
I stayed in one of the units last summer. It trades through II membership that must be purchased separately and it trades easily through them for the weeks they own, which are in June, July and August. That is due to the fact that the Vineyard is popular, a pricey place on which to buy a first or second home, and has limited hotel rooms and even fewer timeshares. You own the *individual room you pay for* for one week (or more) a year.
I own in Wyndham Beachwalk in Waikiki and there is NO COMPARISON in terms of the condition of the units (even though many of the rooms there are also small but not this small.) I have only stayed at Harbor Landing twice. Once was in the late 80's during June (and it was hot and humid and pretty miserable.) The other was July 7-13 in summer of 2013 and it was was much nicer, weather wise, and the units now had AC.
Before owning at Waikiki my own family and I have used II to trade my mom's weeks several times, always getting exactly what we wanted. Compared to the units I have traded into, many of the HL units are like small prison cells (to me.) The one my mom owns in July is like that. It literally is the worst room on the property. It is one very small room with a *tiny* bathroom, a small dresser, and no closet. There is no where to place the daybed back cushions but the floor in the middle of the room or in front of the AC. There are two short twin beds, and the maid makes them up so the face the TV. That's all fine and good but it literally puts one person's head an inch from the door opening. The window looks out onto a parking lot, it at the end of a hallway that is not visible from the lobby and the room has an entry door to the bldg. right next to it. It was impossible to get the maid(s) to keep the shades closed during the day when we were out, so we were lucky the property is small and the Vineyard is fairly crime free cause you could clearly see into the tiny room and who was or was not there. The other things are: 1) its not a big, disciplined team. There are two maids. If you sleep later than they want to stay, which seemed to be between 12:30 pm and 1:30 pm depending on the day and how many rooms were filled, well, you will not have your towels changed or your bed made that day, and 2) that they maid cleans out the communal kitchen saturday mornings over an hour BEFORE THE WEEKLY CHECK OUT TIME. She starts by emptying the food out of the fridge. And dumping it into the trash. I had veggies, fruits and other snack foods and drinks I had bought that was left that I was planning to bring back on the ferry (we brought a car) and pricey lobster dinner leftovers from a restaurant we went to the night before. Ooops. Gone. No apology from the manager, either. Management is quite lame compared to the kind of hotels and timeshares I am used to.
They have decent, free coffee in the lobby, but they take it away at 9 am sharp. SHARP. There is usually someone at the front desk, but when it is the property manager, she spends a lot of time leaving and running to nearby places like the convenience store next door (at least she did when I was there.)
Some rooms are larger, have closets, and some even have a tiny efficiency kitchen and/or a walk-in closet. One of the rooms my mother has in June is like that. Each room is somewhat unique. The communal kitchen has lots of space and nice quality cooking pots in a wide variety of sizes, and enough so that everyone who wants them can use them.
It's not on the beach, and it's not got a pool or hot tub. I would have been unhappy without a car, because the places that I liked best on the island were not the crowded towns/beaches, but the far-off, more low key beaches.
The town itself has VERY few restaurants that serve alcohol, because apparently they don't want it to become a "party town" like Edgartown or Oak Bluffs. Most restaurants close before 9 even during the height of the summer season.
All this said, the TS does have its own sort of low-key charm, mostly due to the really nice BBQ grills, patio tables, the communal kitchen and the fact that the owners seem to use their units and so come back year after year and so are kind to each other, and friendly, and due to the kind of place it is, they are pretty homey and unpretentious folks, too. The place is walking distance to many restaurants, there is a gym in the hotel across the street with a steam room, a large indoor pool and a jacuzzi, and nice electronic fitness machines. As a non-member and non-guest at the hotel, you can pay by the day, by 20 uses, or by the week or month, and the rates are very fair. There is a decent public bus service on the island that goes most everywhere but some places take a while to get to and service to those places doesn't run that frequently.
I wanted to walk out after seeing the room last July. And the room could not be traded for a better one.
I saw one for sale online this week. $6K. Would I pay that for this place? Hell no. My mom paid less than that total for 3 weeks way back when. I paid only $900 including selling price, transfer fees, and closing costs for 308K points EOEY at Waikiki Beachwalk. And knowing what I know about getting cheap or free units from others, I wouldn't think of paying 6K for any TS anywhere. It's too easy to get something else nice then trade.
But, "Martha (the island)" won me over, big time, and has stolen my heart. I will go back to this resort, probably this June (when the room we can use will be a tiny bit better.) And I live in Hawaii!
In the end, I would say if you are used to motels, you would probably be fine here. If you are used to resorts, and think that Harbor Landing is one, because it is a TS..well, it couldn't be further from the reality.