Welcome. Yes, boating can be both relaxing and exciting especially on a boat as versatile as a MacGregor.
1. Maybe you can try renting a boat for a day to see if you get dizzy. Better to learn before you buy. Boats rock a lot and after spending several days on one, I get the "sea legs" and feel the motion.
2. There are boat surveyors, much like home inspectors that will go over a used boat and look for possible problems. But as with home inspectors, there is only so much they can see and there are no guarantees. With that said, the Mac is a fairly simple boat with few things that can go wrong, but if you don't know anything about boating it's best to have an expert check it out. Then you could buy new as I did probably for similar reasons. I didn't want to travel 800 miles to pick up a boat to find something wrong to break the deal. I know the engine is being maintained as is everything else.
3. I bet you could find a Mac close by. Hopefully an owner on this forum might live close to you. Where in Virginia are you? Maybe post a thread. Also, drive down to marinas and such and look for one. Maybe you will luck out and find someone willing to give you a look. I had a guy on the lake follow me into a cove. Then he walked up to us. We were thinking, "This entire lake, why does he come right up next to us?" Then he asked us about the boat saying he was in the market. I was glad to let him have a look and answer questions.
4. We hauled our stock M aluminum trailer from Seattle to Montana without any problems. Our lake is 90 minutes on fast highways and it works just fine with out truck towing it. Your 3500 will probably tow it like it's nothing, however as mentioned above, adding another axle isn't a big deal.
5. Good to plan ahead. It also gives you more time to research it. This board is fantastic and where I started. All the information I found here helped me make my decision to buy a Mac. Roger Macgregor should pay for this site because it was responsible for at lease one sale (mine).
6. Take a boating class. I taught several USPS courses and they do a fine job.
here is a link to find one close to you. Many of the people taking our course were shoppers and didn't own boats. You can also meet other soon to be boaters and learn from them.
QUESTIONS:
1. Take a boating course and you will learn to read charts and know the answers to this. We just got back from a fantastic weekend on the water. Our favorite times to be out are in the evenings and mornings. It's so peaceful and relaxing. When it gets dark it's so nice to be out there away from everything.
2. I hear ya on the crowds. Find out where other ramps are. You might find a less crowded one in a place you didn't know about. Also, try going during the week instead of a busy weekend.
3. Headroom in the rear berth? Not much. It's been compared to a pizza oven. This is only a 26' boat. For a boat its size, it's very roomy. Compared to a camper, it's tiny. I can sit (like the girl in the brochure) with lots of room. The rear berth is pretty big, but the foot is not tall.
4. Seatbelts, no. You don't want or need to be held down. There is other safety gear like life jackets that work well.
Boating and sailing is not for everyone. You need to get out on the water to see if it's for you.
I've owned both sailboats and powerboats. Powerboats stay flat better and have more room, but you get bored pretty quickly unless you are into water sports. Sailboats, because they must sail, are rounder and have less room and rock easier. But they are more fun and relaxing. After a stressful week, we spent the whole day Saturday sailing. We used little fuel, could carry on a conversation and enjoyed the day relaxing in the breeze. At night we anchored, barbecued a fantastic dinner with some nice adult beverages. We watched the sun go down on the water and proceeded to stargaze. Morning coffee was greeted by birds and a calm breeze. Now that's living. Later in the afternoon t-storms blew in. Unlike other sailboats, with the Mac we were able to "put the peddle to the metal" and get off the water just before all hull broke loose.
The Mac is a compromise boat. It doesn't sail great and it doesn't motor great, but it allows you to do things neither a powerboat or keel sailboat can do. Plus, you can trailer it to places others can't.
Get some education, read this forum and ask questions. If sailing is your thing, you will find it extremely pleasurable.
--Russ