Just posted a question about a possible purchase of a Helmsman 38E. I've been sailing for 40 years, 13 years in the Bahamas and the rest of the time in the Pacific Northwest. (the last 21 years in a Catalina 34). We've spent every summer since 1986 living aboard a boat traveling full time only 2 1/2 months every summer. Am quite apprehensive about entering the trawler age, and know I have much to learn. Nervous as heck would be an understatement.
Capran have no fear. As an ex-sailor myself, I can tell you that with all that sailing experience, apart from the nuts and bolts differences over looking after, servicing, and using a much larger engine, and a few other differences, you will find the transition a breeze.
The sheer joy of just being able to hop aboard, load the necessities, (will be much the same), open the seacocks, (important..!), then turn a key, drop the lines, and away you go, with no mucking about over sails, halyards, etc, is something you will marvel at, and wonder why the heck you didn't do it sooner. Then, the first time it rains, or the wind really comes up, or both, and you are warm and dry and don't have to reef the sails, and can go in whatever direction you wish, (within reason - sometimes it is more comfortable to adjust the plan a bit), you will have the biggest smile on your face ever..! Handling the vessel, coming from sail, will often just seem too easy, especially as you are used to handling a similar sized vessel with a much less powerful engine. Just be aware the windage on the superstructure will be greater, and allow for that. However, the huge amount of extra room inside will make it all worthwhile.
