Many of date begin on dating sights. Most profiles include question about marriage, children, etc. One question you can use is: "do you believe in love at first sight?". It seems a harmless question but it revieals important information. Is your prospect a realist or idealist. Another caution to consider, especially if you have money, is that some tell you what they think you want to hear. You must remember that all relationship's are investments. Some pay, some cost. It's your decision when to call it quits. Having an open eye to this can direct you to healthy relationships. I have found that people who live in reality are easier to relate with. I can speak honestly with them, find their expectations of me and negotiate weather or not I can meet those demands. The opposite applies as well. Life is short, too short to waste is distructive endeavors. Time lost can never be recouped. Sounds cold I know but saying no, especially to yourself is freeing.
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I agree with you that all relationships are an investment and we all need to look at it that way. However it is an investment that is difficult to determine sometimes whether it will pay off or not. The key is as you say, to be honest with yourself about you and the person you are dating. This way you never really get surprised. Speaking as someone who has been in a ling term relationship and am exceptionally happy, I can say it all comes down to communication. We are very different in age, culture and many other things, but we have an agreement to talk about whatever is bothering us. It took some time to get this to really happen but now it works. Mostly because we both respect each other and want the relationship to be on solid ground. And also we are clear about what we each want and what the other wants. And finally, what the other wants we each want for that person. Not easy but the alternative which is getting ont he dating merry go round, is much more challenging in my humble opinion.