We are a family of 5 and have a 2-bedroom timeshare. This worked great before we had kids. After kids it has been fair to midland. It really depends on WHERE you want to go. Some years are ok, but with advanced planning other years have been good with an occasional great trade. With such a large family, I wouldn't buy a timeshare regardless of cost. Finding a multi-bedroom unit in a place you want to visit and at the time you want to go can be difficult! The exception would be if you always visit "XYZ" in the summer, then you could purchase a timeshare at "XYZ" for the week you want.
I own at a resort with relatively inexpensive maintenance fees. Between my maintenance fees ($883/yr), Interval International membership ($99/yr), and the exchange fee ($219) I'm into it $1202/yr. This is awesome for a week's stay in a 2-bedroom, but I'm limited to the places/dates available through II (or RCI, but I don't belong to it.) There are some places like Yellow Stone Nat'l Park I'd like to travel with the kids that have no available timeshares nearby that trade in II. Other places might have timeshares, but not many get deposited into II. One problem I've found is a lot of folks split their larger units into two smaller units when depositing their weeks into II. This works great for them because they get 2 weeks of vacation for one maintenance fee, but it means slim pickings for those of us needing 2+ bedrooms! My parents frequently travel with us bringing our travelers to 7. My experience has been that most of the 2-bedrooms only sleep 6. I love trading into Marriotts because theirs usually have double beds in the 2nd bedroom accommodating 8. However, I'm not a Marriott owner so not only do I have to have trading strength to see the Marriott, I have to hope the Marriott owners don't snag all the larger units while they are under priority view.
The fact that you homeschool is a bonus because you can probably travel shoulder season or low season. You should see more availability during those times. Shoulder season can be a great time to travel, but in some areas of the world low season would be very unpleasant due to weather. Even with a family of 5, I've been toying with the idea of either upgrading my timeshare to a 3-bedroom Marriott, or getting rid of it all together. I've been dragging my feet on the 3-bedroom for the reasons mentioned above, but I don't want to get rid of it (yet) because it has been great for places like Orlando and my kids are still into the theme parks. I've also debated doing inexpensive vacations by camping every other year and using the savings to splurg on a nicer vacation the other years.
I own at a resort with relatively inexpensive maintenance fees. Between my maintenance fees ($883/yr), Interval International membership ($99/yr), and the exchange fee ($219) I'm into it $1202/yr. This is awesome for a week's stay in a 2-bedroom, but I'm limited to the places/dates available through II (or RCI, but I don't belong to it.) There are some places like Yellow Stone Nat'l Park I'd like to travel with the kids that have no available timeshares nearby that trade in II. Other places might have timeshares, but not many get deposited into II. One problem I've found is a lot of folks split their larger units into two smaller units when depositing their weeks into II. This works great for them because they get 2 weeks of vacation for one maintenance fee, but it means slim pickings for those of us needing 2+ bedrooms! My parents frequently travel with us bringing our travelers to 7. My experience has been that most of the 2-bedrooms only sleep 6. I love trading into Marriotts because theirs usually have double beds in the 2nd bedroom accommodating 8. However, I'm not a Marriott owner so not only do I have to have trading strength to see the Marriott, I have to hope the Marriott owners don't snag all the larger units while they are under priority view.
The fact that you homeschool is a bonus because you can probably travel shoulder season or low season. You should see more availability during those times. Shoulder season can be a great time to travel, but in some areas of the world low season would be very unpleasant due to weather. Even with a family of 5, I've been toying with the idea of either upgrading my timeshare to a 3-bedroom Marriott, or getting rid of it all together. I've been dragging my feet on the 3-bedroom for the reasons mentioned above, but I don't want to get rid of it (yet) because it has been great for places like Orlando and my kids are still into the theme parks. I've also debated doing inexpensive vacations by camping every other year and using the savings to splurg on a nicer vacation the other years.