It seems that this forum attracts a lot of not-yet boat owners.
Some of them seem to be chasing a dream, something like this:
They plan to find a low engine hour trawler that has been perfectly maintained, hopefully less than 10 years old, available at a heavily discounted purchase price. Having previously navigated around a lake a few times, they plan to immediately move-aboard and "do the loop".
What's the best way to provide newcomers with information without becoming a dream-killer?
I think the best way is to provide a variety of honest answers from different viewpoints. Sometimes that means encouragement, sometimes questions, and sometimes it means killing a dream based on unreasonable expectations. We've even had some recently where safety was a serious factor and that's where I feel the forum has a significant responsibility. I see people encouraged on Cruisers forum to proceed with dangerous and risky plans and I find that to be irresponsible. One just shouldn't encourage a non boater to buy a 20' sailboat and start a circumnavigation without any training. I think here we encourage most newbies, while trying to help them have a realistic view. There are very few that are offered strong discouragement and when that happens, it's generally for their safety.
I think we need to listen and to ask for enough information to offer intelligent advice. Then we can generally provide a path or means for them to achieve their goals. It may be far different than what they anticipated but realistic. If they ignore all advice, that's their right, but when they lash out at forum members whose advice they dislike, then they are wrong. You come to a forum and post, you'll get opinions and that includes some you may not like but that's part of it. If they are respectful to forum members, then they'll be shown respect, but those who disrespect the forum or it's members, deserve no respect themselves.
The goal is to try to give them the information so they can make the decision that is right for them. If that decision is financially unwise, as long as they're informed about the cost, that's their right. All boats are financially poor decisions. If it's something they aren't qualified or trained to do, they need to be advised how to get there. If it is unsafe, they need to be strongly discouraged. Each person must be treated differently.
I think the vast majority of persons asking do so very well and they get a wide variety of answers, altogether very helpful. For those discouraged by forum members talking about costs or maintenance or other facets of the reality of boating, if they're going to give up the idea that easily then they were provided a service as they surely would have given up at great cost to themselves and serious trauma had the tried.
There are a lot of disgruntled boaters and former boaters out there who say "if I'd only known" and follow that talking about the money or the stress or heartache they would have avoided. Our task is to inform so they do know. If that kills a dream, the dream never stood a chance of being realized.
It's hard for us to recognize that boating isn't for everyone and if we only paint the rosy picture of boating as we experience it, then that's not enough.
I love reading all the different answers to one newbie's questions from a wide variety of TF members. I think it's the collective nature that makes it good. One person will discourage a boat in need of a lot of work while another will talk about the work they did and how they love the boat they bought in similar condition. We don't know who the person asking is most like. There are some here who love working on the boat more than boating itself while others of us who do very little working on our boats.
I remember when we first posted on another forum asking for advice on boats of a certain size. We were told if it wasn't Dutch, it was no good. We were told if it wasn't steel, we were going to run over a container floating at sea and drown. We were told the wiring on all Italian boats was horrible and that all UK boats would have spidering in the gelcoat. We had to sort through it but it was all valuable, just some more than other. On one brand we saw reference to a lawsuit on just the model we liked and read the entire set of legal documents. Then on the builder we found ourselves leaning toward, we found several people on the forum who had run their boats extensively, many boats over many years, and we found no one with experience on their boats who didn't like them. However, that doesn't mean the other opinions weren't valuable. Sorting through them all, evaluating them, thinking about them, all helped us make the best decision for ourselves.
People need to receive many opinions, both the positive and the negative ones. Perhaps they need to watch members argue among themselves. Even your best friend with 30 years of experience can lead you down the wrong path for you. I have a good friend who is a captain and if he had his way everyone would buy a Sportfishing boat. I won't buy a boat without a lower helm. I have a captain friend who disparages all Italian boats. That is based on bad experiences with a couple of brands, but we own Riva and manage Riva for members of our extended family and we've had no issues and love them. Now, that happens to be one brand he lacks experience with.
If all you want is to ask a question and get the answer you want, then I'd highly recommend asking it to a mirror and not in a forum. If what you want is an open dialogue and a combination of encouragement but caution and as much information and as many different opinions as possible, then this is the place.
As to your example of lake to loop, most of us here have made great leaps. If you're like us, you wouldn't trade the boating life you have now for anything, but you also understand the path it took to get there. I have 30 years of boating, 99.9% on a single lake and going from 17' to 30'. I was not in any way qualified to safely get out on the ocean nor to even buy a boat. My wife and I dreamed but then we asked "How?" We looked online and read and we signed up for classes and then we were told we needed hands on training and from there it took off. Everyone here had different paths and experiences and when they respond those do influence the responses, but it's all about helping the newbie find their way. For the occasional newcomer who feels they already know it all even though facts say quite the opposite, then frankly until they accept otherwise, no one can help them. And as to their dreams, no they aren't dreams. They are fantasies and there is a huge difference.