A bit of a late reply, but I just came across this. I have enjoyed reading your ramblings. I'm a bit below you on the pay scale - comfortable but still definitely working for a living - saving and planning for retirement at some point, so I'll have time on my hands then for sure.
Romantic relationships seem really important to you, so that's what I will talk about here.
Once I gave relationship advise to a woman I met during a layover in an airport who was heading off to a political party convention of all things. The only thing I could come up with kind of stuck with me - "Find the one you can't live without. Then.... don't [live without them]". I've been pretty lucky in that department - coming up on my 25th wedding anniversary next year.
A friend of mine met the man of her dreams - they are still together to this day I am sure, though I have not seen them in many years - at a gaming convention of all things. Met and talked and hit it off and stayed up all night talking. And that was that.
What I'm trying to get at with my rambling is that when it happens it just happens. And if you know them enough to trust them you can trust them with anything - you just know.
My advise to you is to get out there on the road like you don't have much in the bank, and just meet people. This I know you think is dishonest, but bear with me. Take the time to get to know her - find the ONE man - and during the course of a year play all the "what if" games. What if we won the lottery - what would we do? Then make it happen - concoct your own lottery, or contest, or drawing, or whatever, and "win" a couple of million dollars.
Then do with her all the things you'd do in that case - that will be more fun than you can imagine. And after a year of that - if it hasn't all come unglued - come clean about everything. And she will not care one bit - if anything she'll think it's the most romantic thing she has ever heard of.
That's how I'd do it.