Our family, two parents and two kids, both in high school now, have really enjoyed timeshares. we bought about 18 years ago. Owning timeshares has driven us to always take many real vacations. Sometimes these are in our home resorts, sometimes in II exchanges, sometimes we've rented out our units and rented elsewhere. However, it has anchored the vacation planning cycle.
The only hitch in this long road was a 'trader' we purchased initially. It was a relatively inexpensive resale, from Marriott resales, at their salesman's recommendation (Harbour Point, HHI). It was a waste of time, energy, and money before we knew it. I recall we got a couple of decent trades that aligned with our usage needs. These were off-season or pre-school age. Then, deposits started building up in II. I gave away a couple of off-season usage / low-level resort weeks to family. Eventually, we disposed of that timeshare. We liked HHI by the way, but not that resort or its ability to trade.
Early on, we ignored the school schedules sometimes, for at least one vacation. We had a school tell us in no uncertain terms that this was unacceptable - with the older one in about 3rd grade. Since then, we always align with the school calendar, though we missed a day once or twice due to the travel schedule.
Our other units, all Marriott, peak season, primish views, (aruba ocean view, myrtle ocean front x2) have traded quickly and successfully every time. My problem is the mostly downgraded unit types we got on trade. I like a solid view of the main attraction, usually a nearby body of water. I don't want to wonder until check-in whether I'm looking at a parking lot, playground, or the ocean.
The prime-season/prime-view units do trade easily though. If II solves the unit-view-type visibility problem, I might check it out again. More recently, we added/enrolled in the points program, which isn't as cost-effective but gives us the flexibility and choice we want.
I recommend buying stronger to trade and that you might actually use occasionally. I think the other advice here is valid too and they are very knowledgeable. However, I wanted to convey trade maximization is not for the faint of heart, picky, or schedule constrained. I also believe it is getting a little more difficult each year to make great trades happen. Persistence and flexibility are key. A clearly good enough trader will help enormously. I recommend not trying to squeeze every bit of trading power out.