Keels aside, does anyone else have concerns about a spade rudder? I know most boats come with them nowadays and that might imply that they are fine, but people still point out the safety benefits of skeg hung rudders when talking boat choices.
Bit of a "yesterday" debate as just about all the designers and builders who were advocates of skeg hung rudders in the past have now gone over to spade rudders. Some like Frers and HR have even adopted twin spade rudders! While there are arguments in favour of greater support for the rudder you have to remember they came in at a time when long keels were giving way to shorter keels and rudders moving aft. If you look at early skegs they had to be strong because rudder loads were high (mostly unbalanced rudders) and stocks small diameter. Over time skegs got shorter and rudders given balance below the skeg to reduce load to the extent they became almost spade rudders with an external lower bearing. Not a big step from there to a full spade rudder.
While the theoretical benefits of a skeg remain, in practice spade rudders have been around on offshore cruising boats for well over 20 years. Apart from some well known design disasters such as the composite stocks used by US Hunter they seem to have proved adequately strong and reliable.
I don't know what other boats you have considered, but if you look back the 1980s were the heyday of the fin and skeg with production boats like Moodys and Westerlys in the 35-45' aimed squarely at the offshore/ liveaboard market. 20 years later they had all just about gone and boats like the Vision had filled that sector of the market. In the premium end it took a little longer for a similar transition. Looking at the ARC entry lists over the years will show the evolution clearly.
Buying used rather than new gives you an enormous almost bewildering choice. With your budget you could get a premium 40-46' like a Bowman, Oyster, HR, Malo, Najad, Contest etc from 80's early 90's or a later Moody from the fin and skeg era or a newer more modern production boat like the Vision. However, the initial purchase price is misleading as the key figure is the total of buying plus the replacements, upgrades etc to get it how you want it. In general, the newer the boat, the less you have to spend post purchase.
There are of course lots of other issues to consider apart from the financial. Older boats tend to be less spacious, have smaller cockpits and more staid sailing performance. Sorting out what is important to you is part of the fun. Doing it for real rather than day dreaming can be daunting, but I guess most in the end come to terms with what is best for them and don't regret their choice.