Tanzers tend to be nicely made. I looked up the picture and specs on the 16and it looks nice.
Same hull as the Flying Scot??...aren't they a 19 footer? Has similar appearance though.
What year is the boat you're looking at? They starting making the 16 in 1963. Old glass can be good glass, but it should be reflected in the price.
In my opinion the price is on the high side. With a $2700 budget, I would think there'd be a lot more you could look at. Definitly check the Tanzer 16 owner's website and find out if there are any problem areas, like leaks around the centerboard, etc. Probably possible to find out a little more about what they sell for.
It is NOT too big a boat to start with. A sixteen is an easy boat to trailer and launch. There's not too much of a mast to deal with each time you rig
As much as I love a classic day sailer, the one bummer they all share is lack of a place to pee...other than putting it over the side. Mixed company can make that impractical. Once you leave the launch ramp, your adventures may be limited by the smallest bladder on board, unless you have convenient places to either beach it or tie up.
A boat like a Catalina 22 or an O'Day 20 can be an ideal starter
boat, but they're a lot more to haul and setup is more involved than with a 16 footer. Taking it apart after a long hot day with maybe a little sunburn, etc. can sour you on trailering real fast.
Catalina and Hunter have both made 18 footers (approx) that have small cabins that can hold a porta pottie and are small enough to trailer and rig
As you look for a day sailer (no cabin) you really want to throw out a low-ball offer and be prepared to walk away. I can tell you from experience that when you sell one, they can sit for quite awhile and command less money than you'd like. They seem to be both a little hard to find and a little hard to sell.
, whatever you start with, you're very likely to sell in a couple years as you either quit or refine your needs and replace with another boat. Price, price, price.