I made the leap, and I made the leap while buying a resale contract as well; talk about early onset add-on-itus. So that's what I would do. Here's my rationale, which may or may not work for you.
I bought a 75 point direct AKL. Total cost was $13,800. The premium chart I posted is a helpful guide, but throw that out the window for this specific rationale. Do I plan on staying at AKL? Yes, but AKL is easy to book so there's no true 11-mo advantage. My resale points will also be much cheaper (if it passes) so I plan on using my cheap resale points for all of my vacations; which will come in at a much cheaper $7.20/ppt (all ppt is time adjusted values) vs the $10.89/ppt of AKL Direct.
To eliminate any concerns about time, this will assume that I keep it the entire term. As I would want the membership benefit as long as possible. So how do I break even? Easy, if AKL Direct is $10.89/ppt; I just need to commit to renting out my AKL Direct Points all the time. Renting out points fetches $14.50/ppt through a broker; $15-$16 direct on this site. As long as I do that year in and year out, my membership is self-funded. AKL happens to be the most popular rental location; which helps with this strategy.
But let's assume you don't like my time adjusted values, and let's assume I won't be disciplined enough to consistently rent it out year after year. Well, I planned for that too. I can promise I'll follow it for at least one year right? So I'll do that. But let's also assume you want to ask about about my $13,800 and opportunity cost. Good question!
I'm going to list my 75 points immediately. The contract came with 2019 points, 75*$14.50=$1087.50 and will have an additional 75 points within the next couple of months. So before my first round of annual dues, I would already be covering $2,175 ('19/75+'18/75 * $14.50 rental) of it. Since we're factoring opportunity cost...well, I paid for it with a credit card. 0% financing for 1 year. $400 cash back when spending $1000. Plus 1.5% cash back on all purchases. That means come January, I will have $2,782 (rental+credit card rewards & promos) in my pocket that I didn't have before and I haven't paid a thing. Thrown in a CD, by the time that amount is actually due, it would be worth nearly $3000 in a CD - but let's go crazy. Let's take that $2,782 and open a new checking account with a bank of your choice. A lot of which offers $200-400 cash upon depositing a certain amount. The requirement is to hold the account open for 6 mo typically. At the end of 6 mo, I close the account and apply the amount of $3182 to my credit card bill. The amount due of my money at this point? $10,618. Let's pull the closing costs back out of it and make it an even $10,000. That now comes to $133.33/pt - or 75% of the Direct asking price.
That doesn't seem so bad anymore, and quite comparable to the resale market for a small contract. I evaluated it about a dozen ways and it made sense in most of them, so I took the leap.