You won't save any money by purchasing a timeshare in your situation. You will purchase a major headache.
You will have to book in advance or to trade well in advance and there is no guarantee you will get the time you want. It's a gamble, people say. But let's assume you got lucky and made your reservation a year in advance. Two months in advance your boss authorizes your vacation and you go looking for the plane tickets, and - surprise - the tickets for your booked dates are expensive, while a week before or after there are good deals for the tickets.
Maintenance fees go up, sometimes +10% or more every year. Some good Hawaiian timeshares are in the $2,000 - $3,000 range per week and keep going up. And in addition to that you will be hit with special assessments from time to time.
If you buy a cheap timeshare with MFs in $500 - $800 range, your trades to places you want to go will be unreliable. Plus, it will cost you around $100 - $200 in annual membership fees + $100 - $200 per trade. I looked at RCI availability with supposedly good traders and I did not like what I saw at all. You will not reliably get into any decent places with trading.
If you had an experience of buying discount all-inclusive vacations from travel agencies which include flights, nice hotels and all meals, then you will not get anything like that with timeshares.
If you cannot go in some years for financial or personal reasons, you are stuck with your timeshare. You still have to pay MFs, and then have a headache finding a renter.
Now timeshares can be a good thing, if ALL of the following applies to you:
1. You have children and always need 1-br or 2-br accommodation.
2. You can always plan more than a year in advance and your plans do not change.
3. If your trades do not happen as planned, then you don't mind going to the timeshare you own, same place every year, you love the place and it is within driving distance.
4. You believe economy will improve significantly and all current cheap rentals will not be available in the future.
5. You are prepared to pay increasing MFs forever. You understand that if you want out, then you may not be able to get rid of your timeshare when the time comes. Nobody may want to take it from you even for free, so you will be stuck with MFs forever.