I think Wellcraft has gone the way of American auto manufacturers. Selling chinsy plastic looking crap with options like lighted cup holders to the boat show crowd instead of building solid no frills well designed fishing/diving hulls.
Any boat is gonna cost you money. You can get a V20 in good shape for less than the first years depreciation on a new boat. Plus your V20 will turn heads of those who know and those that don't, unlike all those new boats that come out looking like some 3 year old kid's bath tub toy.
I don't have any regrets about buying my old girl, though I think it's good you're not in a rush. Look on here at what different people have and think about what you're really looking for. My next V20 will be an old 1960's Alim hull with an enclosed transom or a Sea-drive model from Wellcraft. Not really a regret, just something I would have done different.