To help sweeten the deal if you can wait, REI carries Tomcats and Outlaws, which means that if you are a member, you can get one 20% off in the spring, if they don't offer a coupon sooner, and you can use your dividend.
As for the vinyl, I bought a used tomcat several years ago, and used it a good bit for a year or two before I found a killer deal on a lynx which is now my go to ducky. The tomcat is now my loaner ducky, but it is still going strong, so that would not deter me.
I also just picked up a solo outlaw for my 12 year old to grow into, and am impressed so far. I like the way it handles with the very limited time I have been in it. I think the issue about draining with them comes from having 2 adults in a tandem, with only a 4 inch floor, that doesn't offer much between your rear and the water. I think the solo can float a single adult better than the tandem can float two, and that the tandem would probably do better with a 6 inch floor. I have some heavier friends that are in the market, and for that reason, I am steering them towards the tomcat.
As a side note, the tandems are a bit barge like compared to a solo, but they do carry more people and stuff. Compared to a raft it will probably feel sporty, compared to a kayak or solo ducky, it will feel sluggish and have less maneuverability.
"If I'm not there, it means I'm dead...or late!" General W.R. Monger