One person operation of 50-100 ft yacht?

It's a shame you are having such a problem with this. As you have probably deduced, small boat captains simply hate the idea of someone without their pedigree being successful at what you would like to do.

Long before you get to the point of needing to know what to look for in a specific boat or type of boat, you really do need to define as closely as possible exactly what you would like to do with the boat, where, and for how long. There are many boats available that make fantastic liveaboards, many more that make great inland cruising boats, and many more again that make really great platforms for island hopping in the Caribbean.

Spend a lot of time defining your dream first, then look at the type of boat that most experienced people use in the situation you define. See if that fits for you. By the time you have that figured out you will have answered a lot of your own questions. Read books written by people like yourself who did what you want to do, in the US and in Europe or elsewhere, learn from them and their mistakes and successes. There is no hurry to choose a boat, there are plenty of them around and one will wait for you.

Good luck and try to enjoy the process in spite of the admiralty.

I Googled this for you with the terms "cruising books" now go set up an account with Amazon.

http://cruisenews.net/db/books.php

Most of what you've written is on point, but as for your first paragraph, you did read this didn't you?

or that he's looking for a first boat in the 48' to 100' range with plans to single-hand on the western rivers.
As for the books, that's nice entertainment, but I prefer a bit more hands-on approach , i.e. get out on the boats. Us small boat captains don't mind anyone being successful, it's the failures we don't like. They bring on damaged property and dead bodies. Rather than going to Amazon may I suggest that the poster spend a lot of time using the SEARCH feature here. There are not many questions a new boater can ask that haven't been answered here. A basic boating class (as was suggested earlier) would also be a good idea as would spending some time understanding charts.

Yep, read every word from the beginning.

It's a shame no one gives the guy credit for having the sense to find out this stuff through being shown a few doors and by getting some support and guidance from the people who are supposed to have all the answers.

I remember telling my parents that I wanted to be an airline pilot when I was 8 or 9 years old. They didn't tell me I needed to hire a pilot, they showed me the places to find information about how to do it. I worked my way into the left seat of a scheduled airline because people alonog the way told me how, not that I couldn't.

I read about William Beebe when I was about the same age and said I wanted to see what he saw. No one told me I had to hire Oceaneering, they told me where to discover what was involved in the process and years later I drove a 2-man sub nearly twice as deep as Beebe ever reached.

Give the guy a lead, not a hobble.

I've seen a lot of realism here and as for a lead:

should get him on the water long before reading sea stories will.

And reading the stories of contemporary real people who had the same idea as his, and how it worked (or didn't) for them will save him asking a bunch of what you see as silly questions. They aren't just "sea stories" of the Conrad, London, Kipling, and Dana variety.

Maybe he will then see that expecting to start out singlehanding a 100 foot boat may not be the best plan.

First, I don't consider any question silly unless asked multiple times by the same person.
Second, although good authors, what relevance do those books have to someone looking to buy a large motoryacht as a first boat that will be used on the Arkansas River? Better a few boating magazines, Chapman's, and lots of time spent culling through relevent topics on Yacht Forums.com via SEARCH.
Third, I think he probably got the idea that singlehanding a 100 footer may not be the best plan and he didn't have to spend 15 hours reading books written 50+ years ago to get there.
And Pascal, What's with the "so dont' lump me in the same "samll boat captain with a new yorker attitude" boat"? I resemble that remark. (Old joke in case you don't catch it.

I bought my first boat in 2009 ... a Bertram 28.
bought my second boat in 2010 ... a Bertram 54

Travelers insures both without hesitation.

Single handed is challenging at times and fun.

I'm sure the insurance company would have had more to say if the price was over $1 million.

On that note you are on your way; the first day towards the rest of a great adventure. Research, learn and come back with any questions. Good luck, and most of all, stay safe.

With your experience level single handing a boat in the 48' range is too much, and the larger even worse. Like everyone else said, find out what your aspirations are in size and usage and go from there.

I would recommend something smaller if you're going to single hand....When you become more experienced then you can decide to move up.........Something like a 42' Grand Banks with twin engines would be a good choice. Easily maneuverable, easy access around the boat when docking with the lower station and wing doors, built well, safe, and will take you just about anywhere you want to go. Even a 32' Grand Banks would be a good choice with a bow thruster. A Coast Guard auxilary class is a good start. Insurance companies will probably not insure you at 48' and above. 42' you may be ok.......

Good aspiration, there is something very satisfying and challenging about living on a boat. I've done it, and loved it. I'm even looking to do a 'floating cottage' now for both Thailand and maybe northern FL area.

I believe some of the advice you been given about strarting out wuth something a little smaller (40-48 range) is good. It will give you more confidence in the learning process, and time to consider what that larger boat might be best for your next step. Plus this smaller vessel may be easier to resell when you are ready to move to that next step.

For some of your initial 'cruises' that I imagine involve canal transits, you may likely have a few friends that would love to go along just for the one/two week experience.

I'm sure if you do some careful looking you can find some deals out there right now. Best of luck to you. GO FOR IT.

Very good advice.

Except you don't need a bow thruster on a 32' GB. And he would learn more about handling a boat if it was without one as well.

He's going not growing into this boat and a 32 GB can be a beast in wind that will test your skill docking. A thruster would probably be money well spent.

The problem with Bow Thrusters is not in their usage, but relying on them.
Only had a thruster on one of my boats & the one time I truly needed to use it.......it failed.
If you can't handle your boat without one, you need to learn to!
They are a luxury.

With twin screw yes, but this is a single screw trawler with a keel. It takes experience to manage that on a windy day, using lines to pivot, etc.