The traditional is a looker and hate to admit but I don't want to sail a boat unless it looks good. I'd like it better if it weren't a "liveaboard", but it appears well equipped. The engine can be a deal breaker if it's not topnotch. I'd pick the features that really matter and select a boat that already has them. If you want a windlass and autopilot and dodger, you'll spend a fortune adding them. Likewise if the boat has an ancient ill wired panel you may find that you just live with it rather than make it right. Again, pick features you really need that someone else already bought. You'll get more sailing and spend less upgrading and repairing. The comments about exponential costs are true. But for a first boat the mid/upper 30 footer range sounds like a reasonable size. Good luck!