Welcome. Having done the coastal thing then the river/lake thing then back to the coastal thing, it is easy for me to see where you are in this. If you can operate a 36' boat you can operate a 44' boat. It is too expensive to take steps because of fear of operating the boat. What is important is the configuration of the boat. Get someting that you can handle comfortably both at the helm and on deck.
Chartering is a great way to start. You can charter different style trawlers or other boats to see what will fit you best. Power Squadron and Coast Guard courses are great, and on the water training can be a great thing. There is a world of info in the TF archives. Use the search feature in the bar near the top of the page to query most any subject.
I envy your search. The shopping process is interesting and fun. Good luck.
Don on Moonstruck
Sabre 42 Hardtop Express & Blackfin 25 CC
When cruising life is simpler, but on a grander scale (author unknown)