As far as small to medium size convertibles go, in Hatteras Yachts you have a choice of the old style 36 (small, but fast with the right engines) newer (relative term!) 36 and 37 (slower but roomier), and the 42, 43, and 45-46 convertibles. The 34s were nice boats but are very old at this point, unless you find a boat that was redone and kept up, which will more than likely belong to one of our members on this forum.
These boats are all so inexpensive now that you will have quite a few to choose from. The best one to get is one that was always kept up and not allowed to get shabby and require a complete refit. If you can find one in the Great Lakes, so much the better; freshwater boats are generally nicer as they are not in salt or brackish water and they have a shorter use season. They are also stored indoors in the winter in many cases.
I would look for a 42 which had been repowered with Cummins C engines- there are a few out there. Or a 43 or 45, repowered if you can find one. I think one is actually for sale on this forum. 36 Series I boats (like I have) are very affordable, and many of them have been repowered with Cummins B engines, the powerplants of choice.
Engines to avoid would be Caterpillar 3116 or 3126, based on my experience and that of my friends. Detroits are fine if kept up but are noisy, slow and use a lot of fuel, which is why many of them have been replaced. Caterpillar 3208s are also fine engines; as always, service history is important.
Have a look on Yachtworld. Avoid eBay and CL- they are no place to shop for a boat. Read Seaeric's posts on the steps to buying a boat, recently in a thread here. I think Pascoe's reviews are pretty good, but he hasn't updated them in ages. Of course, you aren't talking about a new Hatteras, either, so it may not matter.
And watch the for sale area on this forum, because some nice boats have come and gone here.
As far as books go, there aren't really any. I'd suggest getting out on the docks and looking at a lot of boats. Also look at competitors to Hatteras- the comparison is illuminating.