Look you will find good and bad advise here (mine included) 
At 5 months it is not a dire as some are saying here and your looking for a 1 bed room if I read correctly. Studios usually go fast and are hard to come by but there is always wait list. 1br units are easier as you will the higher points needed rooms are always lurking around at that booking window. Also unless your vacation dates always included major holidays Halloween (MNSHP), Thanksgiving, Christmas, or one of the many Running events you should be safe.
Given your dynamics I would be looking resale at OKW( the most underrated of all DVC properties, you cant beat the size of the rooms at this resort my first 2br apartment was not as big as a 1br), SSR, or AKV.
But I really feel it is not as bad as the people are saying here but they are right you have to be flexible, you might not get the "cheap" rooms, the view may not be what you want, may not be the resort that you had your mickey heart set on, and you may have to split resorts during your stay but it can be done. But we want people who join our ranks to be happy with their purchase into DVC.
The only DVC property that I have ever struggled to get into at the 7 month window, and have not been successful is the Grand Californian. They really need to build another in California.
Maybe the thing to try for the first time at a DVC resort is to try to rent point points through like Dave's rental site and a sponsor here on this board at your booking window and see how it works then make a decision to buy or not. Or there is always buy DVC at then book your home resort at 11 months or non home resort at 7 months then if your plans change cancel. Your cancealtion can potentially make someone on the wait list happy just don't miss your banking window or you will list your points for rent and making a rental customer happy either way some or all end up happy. Disney Joy
We love DVC its not right for everyone but if you decide to take the plunge Welcome Home.
My 2 cents

At 5 months it is not a dire as some are saying here and your looking for a 1 bed room if I read correctly. Studios usually go fast and are hard to come by but there is always wait list. 1br units are easier as you will the higher points needed rooms are always lurking around at that booking window. Also unless your vacation dates always included major holidays Halloween (MNSHP), Thanksgiving, Christmas, or one of the many Running events you should be safe.
Given your dynamics I would be looking resale at OKW( the most underrated of all DVC properties, you cant beat the size of the rooms at this resort my first 2br apartment was not as big as a 1br), SSR, or AKV.
But I really feel it is not as bad as the people are saying here but they are right you have to be flexible, you might not get the "cheap" rooms, the view may not be what you want, may not be the resort that you had your mickey heart set on, and you may have to split resorts during your stay but it can be done. But we want people who join our ranks to be happy with their purchase into DVC.
The only DVC property that I have ever struggled to get into at the 7 month window, and have not been successful is the Grand Californian. They really need to build another in California.
Maybe the thing to try for the first time at a DVC resort is to try to rent point points through like Dave's rental site and a sponsor here on this board at your booking window and see how it works then make a decision to buy or not. Or there is always buy DVC at then book your home resort at 11 months or non home resort at 7 months then if your plans change cancel. Your cancealtion can potentially make someone on the wait list happy just don't miss your banking window or you will list your points for rent and making a rental customer happy either way some or all end up happy. Disney Joy
We love DVC its not right for everyone but if you decide to take the plunge Welcome Home.
My 2 cents