If you have $32k and can find a ski week then it may be a good option. Event weeks like New Year and President's day will be even more expensive. The building where the hotel rooms were converted were never sold as weeks. The timeshare building has amazing villas(more spacious and great views) but those will be hard to find. I could see President's day weekend 12 months ahead this weekend. If that is where you want to go every year for now then the cheapest option would be to get resale Sheraton Flex points. You can not go to Maui but Sheraton has an option in HI for Kauai. There is also Avon, for skiing which I saw 12 months out for President's day this weekend. One of the gems nobody talks about is the Florida Jensen Beach property that is in Sheraton Flex. The rear is made up of Arizona and Orlando. The villas at Steamboat ranged from the 4 bedroom to hotel but there were no mountain side or valley view units to book (these are the dedicated timeshare villas) when I looked this weekend. I think these weeks are used by owners and therefore difficult to book although there may be a few in the trust as I believe they were sold for big bucks at the time and I don't know if they were sold out.
You can use your points in Interval but the points cost can be expensive and you cannot upgrade for extra cost like you can with weeks deposited. If you want a 2 bedroom exchange you will have to deposit the right amount of points for the season/demand. To
@sponger76's point you can deposit your Sheraton Flex options into Interval as well and use them within two years if you cannot go one year.
You will not pay the VSN fee because the Sheraton points will not be in the network. You will therefore not be able to convert to Staroptions or Abound. The maintenance fees will be higher per point than owning a week. Just remember that if you get a week at Steamboat it will be a voluntary resort and therefore not come with the option to use Staroptions at 8 months. Getting a mandatory resort and using Staroptions at 8 months may be more risky when it comes to availability. I can however not speak for making a high demand reservation at 8 months at Steamboat as I have not tried that before. Maybe someone else will be able to chime in.
If you can live with the restrictions and booking 12 months out you will probably be happy with getting Sheraton Flex on the resale market for next to nothing.
In short, if it was me and I wanted to go to Steamboat in ski season every year for the next ten years I would get Sheraton Flex because there seems to be good availability at 12 months for most units except the dedicated timeshare side villas. It will have a bit more flexibility in terms of being able to go to the other resorts within the system especially if you book at 12 months you will probably get what you want with high demand being slightly more difficult. You will also have the option to deposit into Interval and although more expensive you can probably get 3 summer weeks for the amount of points a dedicated 2 bedroom ski week will cost in points. Which brings me to another point in the flexibility of being able to book 1-14 nights instead of having to book your whole week and using it at once.
Paying $32k for a ski week may be difficult to get what you want as you will be competing with a small pool of other ski week owners for the prized times. I don't own weeks there so cannot say for sure but this seems to be the case with most weeks based systems. You will be more restricted as you will have to use interval to trade your week somewhere else and Vistana gives a blended value so it may not see everything. The weeks there are not lock of so you will have to deposit the whole thing.
Lastly, I am going to be crucified for what I am about to say here on these boards. If you have $32k and do not have to make a loan buying direct may not be a bad option because you will be able to use your points in the network to book at 8 months at other Vistana resorts (including Maui) not in the Sheraton Flex system and you will be able to convert to Abound points from day one to book at 12 months at other Marriott resorts (including Maui). However, realize that you will not get very many Abound points and if you want to go to a Marriott resort at high demand times or get a 2 bedroom you will not have enough points for a week unless you want to splurge and use it for a weekend but that may not make sense. When you use it for other Vistana stays your 81 000 points will mostly get you a 1 bedroom in high demand times and 2 bedroom in medium demand times. Because you can use it as Staroptions or in Abound you will be able to combine your points by banking forward or borrowing backward which will allow you to combine two years worth of points or even three years if you do both for a big celebration or dream destination. This may not make sense though due to the cost of maintenance fees involved and considering what your initial outlay was on developer points (This is where weeks will always trump points in terms of value if your week is in the system and high demand/season). Only you can say if it is worth the outlay to have even more options but at less value for your maintenance fees and initial outlay.
If you get resale Sheraton Flex points you can bring it into the system at a later date with a developer purchase. Make sure you get the largest package you can afford the maintenance fees of each year, that you can reasonably make use off. Getting a few $1 or free small point packages may cost more to bring into the system later on because Vistana make you bring more money to the table per points package. Before Marriott it would cost $15k for the first package and $5k for the next package and so on. Make sure you don't get a big package that is split into two (I learned my lesson this way) from one person. Things may change and Marriott may demand more money depending on the amount of points rather than per package. Nobody knows but it is good to have all the information so you can be prepared for all the eventualities.
