It will feel quite intimidating going through the process for the first time but will be more than worth it in the end if you find a good one.
It will be important to find an engineer you feel you can trust so get recommendations (they will all have detractors as nobody is perfect buts it's the promoters who count in my view).
Other things you may want to consider are major accident damage (although things can be repaired well by good engineers), the history of ownership (if a plane changes hands often does that mean anything) and cost/availability of parts.
Many of the older fleet have ageing avionics and that will cost a lot to bring up to date.
I bought an Arrow some years ago and have been very happy with it although with the benefit of hindsight I am sure I would have done the purchase more thoroughly! I also think I would have given more consideration to a permit aircraft but am too attached to my Arrow now to consider replacing it.
Good luck.