There is a bit of a mindset difference between power boats and sailboats. Sometimes like oil and water, though I tend to get along with both camps. Trawlers are kind of like a bridge between them. Most power boats are designed with a planing hull, which means as you give it more power the boat lifts off the water and can go as fast as your wallet will allow. Bigger motors and more gas can be given to the boat to make it go faster. Sailboats and many trawlers are displacement hulls and can only go as fast as the water line dictates. There are exceptions, but not a lot for sailboats big enough to retire on. So with a displacement hull you can add more sail or power but the boat will not really go any faster as it is not designed to plain above the water. Now where are advantages to both, but displacement hulls tend to be more fuel efficient and more comfortable but of course much slower.
For me it is a more spiritual decision, as I just love sailing. For others it is a time decision, where they may enjoy sailing but they don't have a week to get to the next destination and want to do it in a day. And for yet others it is a financial decision as you can cruse for much less on a sailboat, cost are a bit more on a trawler and even more on a planing vessel. Hull speed is =1.34 X square root of the water line in feet. So a boat with a 35 foot water line is about 8 miles an hour. Keep in mind that is a Max speed so you are not going to get anywhere fast. Another point is that power boats are generally have more cabin space per foot, also a consideration.
I would suggest taking ASA courses, they have have stay aboard courses where you practice as you learn and experience living aboard. You get a vacation and learn. Even if you decide to go to the dark side (power boats) most of the info is still valid. Rules of the road/safety/weather/navigation are all the same sail or power. I think it is important even for power boaters to understand how sailboat operate and there limitations. Makes for better on the water dealings.
Best of luck and ask away. As they say the only stupid questions are the ones not asked. Generally it is a friendly bunch here (as long as you stay out of the politics and off topic forums!) and many are experienced with power as well as sail, though few admit it!