Ok, I'll have a crack at it.
For question one, why doesn't Bruce Wayne give away tons of money?
Uh.. he does, this is basic Bruce Wayne character trait 101, Bruce Wayne is an internationally renowned philanthropist and the sheer scale of his charitable work requires that both him and his company are worth billions, economics man, it's technical.
I don't see any reason he should beggar himself for charity and considering the amount of times the man has literally saved the entire planet... I'd say the money used to finance Batman is money well spent.
Also his own (refreshingly realist) answer to that question can be found in a conversation he has with Jezebel Jet at an art exhibition, I'll leave it to you to find it (you know the one, it's about 5 minutes before a bunch of ninja Manbats attack, "alarming twist").
Powered armour?
Dude... He's already wearing it.
Kevlar/nomex reinforced suit, plating underneath, cooling systems, the cowl contains AR HUD, communications suite and some nifty gas vents, the cape as we all know is flame-proof, weighted tips, ribbed and capable of gliding and slowing descent.
The gauntlets contain a wrist top computer (ref: TAS), sap knuckles, probably more but I'm not going through every book on the shelf here just what I can remember.
The entire suit contains enough of an electrical charge to knock a person out cold and obviously therefore can be used to power external devices.
And all that is before we even mention the belt, which I'm sure we all know is not just a bunch of pouches with gadgets in them.
All of the above is supported by many many Batman stories over the years, details may change but I assure you the message is clear...
Do not be so naive as to think this man is running around in just a spandex suit with a tool-belt around his waist.
But if you do think that, Bruce would be satisfied because that's exactly what he wants you to think.
As for why he trains youngsters instead of adults... Bruce never asked for nor sought out any of the Robins (with the debatable exception of Jason).
They all came to him through circumstances of fate (and writing) and after Jason died he vehemently resisted the idea of ever taking on another Robin, I'm sure you can remember the hell Tim went through to get accepted.
Dick wouldn't have become Robin if Bruce Wayne had not gone to the circus that night, just dumb luck or fate that Bruce Wayne witnesses a boy go through exactly what he did... It's not a great stretch of psychological reasoning to see how that kid ended up as his sidekick.
Jason... Well as I said, debatable and not exactly well written (more like "we want a new Robin, write any old crappy reason for them meeting, just do it fast").
Damian is his son and became Robin in his absence.
Steph... well let's not even go there. >.> But those were exceptional circumstances and had a lot more to do with Tim leaving than Steph joining (or Bruce wanting her to) at the time.
Anyway I don't really count Steph as a Robin, she was just a rebound (sorry Spoiler fans!).
Anyway, that's all just my opinion, agree or disagree it's always fun to think about these things.
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