Hello from new member contemplating “the jump”

Greetings! New member here. My wife and I have owned five sailboats over the last 34 years or so, ranging from 16 to 40 feet. We are in our mid-50s and returned from an overseas assignment about a year ago, where I got to do a lot of sailing. We are almost settled down enough now to begin the search for the next boat (sold the 40 when we moved to Australia), and have decided to bite the bullet and enter our “trawler years” lol! Anyway, looking forward to listening, lurking and learning as much as possible here on the forum.
Cheers!
Rusty

Welcome aboard there, shipmate. You will doubtless be much aided in your search by reading through all there is to offer here. Go down to the Galveston Yacht Club and wander the piers until you come upon my boat Calypso (GB42), homeport Panama City. You might be a bit confused about my living in PC with a boat in Galveston, but that's cuz I sorta loaned it out a few years ago to a new custodian. Anyway it is the culmination of a few decades of my efforts to perfect the perfect trawler yacht. And that's all I can offer.

Welcome to the Forum Rusty (and of course your wife)!
It sounds like you two have lots of experience boating (sailing) and operating a single engine craft. Therefore, unless you are planning on a fairly large (45 feet plus) power boat, I would suggest staying with a single engine. Most often on the sub 45' trawlers, twins can make maintenance difficult due to lack of engine room space. Of course there are always exceptions, but generally speaking.....
My wife and I made the same move (from sail to trawler) a few years back. The biggest surprises for me were how much more maintenance there is on a trawler compared to a 37 foot sailboat, and the differences in "close quarters" boat handling. We had an experienced boat captain (from a 100 foot plus yacht) come aboard to give us "hands on" lessons. That really helped, especially since my wife and I switched roles. She now does almost all of the docking and close quarters boat handling.
Try to view as many boats, models, makes, types, etc. as you can. Look at them as to how they will meet your needs, desires, etc. and especially from the perspective of how you plan to use the boat. For example, weekend trips, or months at a time. Guests often, or hardly at all, etc.
Make lists of "must have", "nice to have", and "don't want". For us, on our don't want list were: twin engine (double the maintenance and repair cost, lack of access for maintenance), exterior wood trim (don't want the "extra" maintenance), and screwed down teak decks (if they haven't leaked yet, they will, (hundreds of screws) and repair can be very costly). These lists coupled with your dock walking, boat shows, etc. will help you narrow your list of boats that interest you. Then, look at them very carefully especially from an ongoing maintenance (especially access) point of view. Enjoy the process and good luck in your search.
PS. Keep a fairly sizeable budget for upgrades, repairs, "making it your own", and getting maintenance up to date. This one surprised us a bit, and not in a good way and our boat was in excellent shape!

Welcome aboard. Good luck in your new boat search.