Complete back of the napkin math here, but you would be looking at the following over 5 years:
Purchase of Willow Ridge (closing costs/XFR fees): $500
5 years of II: $500 (assumes you do not purchase multiple years and get a savings)
5 years of MF (at about $500 per year for EOY): $2500
Total outlay: $3500 (about $700 per year)
This is to get into II primarily so you can book Getaways
So you need to get $700 in value every year on average to break even.
And then when you want to unload it, you will pay about $500 (listing, closing costs), and possibly throwing in $500 MF.
Offset possibilities:
Rent out Willow Ridge every other year (research the rent range).
Split the Willow Ridge week ($Fee) and try to exchange it** (2x$Fee) into two other resorts. Your offset = What it would cost to rent into these - Split fee and Exchange fees.
Getaways. Your offset = What it would cost to rent into it - Getaway fee.
Other options:
Just rent where you want to stay. You'd be surprised how inexpensive it can be. Last minute rentals can be great deals.
Avoids: Escrow, II dues, exchange fees, Getaway fees, Maintenance Fees, Special Assessments, having to unload it later.
One of the most basic pieces of advice on TUG: Buy at a resort where you would stay at least 50% of the time; don't buy where you would not stay.
** Willow Ridge has no trading power in II. You are very unlikely to deposit it and get a Maui in exchange. The strategy of most WR owners is to split their unit and do *daily* searches on II for dates that are 59 days or less from your date of travel. During this time, all possible exchanges are visible (they are visible to everyone in that travel window, regardless of what they own). So you are competing with everyone, but you can see all properties. This is when people snag the 2BR Mauis with a Studio WR. They appear at 5AM and are snatched up by 5:02AM. This was my experience. I fully acknowledge that others do far better. If you are comfortable with this, it may work very well for you.