Answering some questions

I have been asked so many times mostly by SB's but some prospective SD's as well: where do I meet these women, how many have I met in total, how do I negotiate with them, what types of deals have we had etc. Here are some examples that come to mind right away. By the way, I am a firm believer in the school of hard knocks, i.e. you can't just say to someone do this, or do that, and if that, then go do something else. You just have to try and see what works, because every person, situation, and chemistry is different from the next.

Where do I met them:
Sometimes, in the middle of the street, literally. Strike up a conversation, and either wipe out, or go for coffee and talk more. The profile: A person 20 to 25 y.o. If they bite, I know they are attracted to an older man, and all that comes with it. Another favorite, is hostesses at fancy restaurants or hotels where business people hang out. I have found these women pretty easy to chat up because they are the friendly and social type anyway. Bring up the subject of SD, or better yet 'mentorship', because just mentioning SD has bad meanings to some people.
The best age: 27+ end of story. More maturity, life experience, don't live with mommy and daddy anymore, don't have 'sweetie pie' written on their underwear like Lil' Kim did, and have real life responsibilities.
Some others I met through craigslist when that place was good. Now days I am not sure if that really works anymore. Too much spam. Sd4Me: bunch of weirdos, but some of it is good. I don't have a profile there, but just tried it for a month, some time ago. At least half the emails I got were from professional escorts masquerading as SB's. In the very early days I did meet some bona fide SB's through match dot com.

What do I give them and what do they ask for:
Some have asked for several $K per month as an allowance. I gave it to those that would save that money for investing, or at least pay off debt. I did not give any allowance to those who I felt would blow it all on new shoes, or to support deadbeat boyfriends or roommates. And believe me guys, many SB's do just that: take money from one guy and pass it on to the next. So I would feel totally silly if I were to subsidize someone like that. I can just picture it: Next thing they would ask would be a 401(k) and health insurance.
The subject of allowances is very touchy with me, because it almost lead to a marriage break some years ago, for reasons I will not go into. So, once bitten twice shy as they say. Plus, it also has a bit of moral implications as well: shouldn't that be reserved for those you love and trust the most? And most SB's I have personally met don't fit in that category.
Also, how they ask is very important: I tend to be a person who gets ticked off rather easily by small, imperceptible things. So if someone comes in with a swagger and says, 'Yo bro, I want $4K per month for the pleasure of my companionship, and you are lucky to have me', I would tend to finish my drink and get up. If she talks about it in a more reserved manner, even if she has to act, then I would probably give it to her. But then again, at least half the SB's out there are scammers (just as are some SD's, I am sure). The true SB, like Diggs, for example, will hang around. But the scammer will take the money and disappear. So that's why I don't like allowances. I don't really know at first if I am dealing with a scammer or not. I used to deal with enough scum balls in my professional life, so in my personal life I would like a break from that.
Many SB's have asked me to pay their rent (which I have done), others just take care of their bills (which I have also done). One asked me to get her a rather large electronic device, but I told her she will have to fly over to my city of residence and get it in person.
So it really depends on the SB, and each individuals needs at that time. I generally like to size them up, so I let them do all the talking. You can tell a lot by how one explains things and looking at their thought process. If they pressure me into saying something, I tend to bring up the last arrangement I had, if I liked it, and use that as a starting point. It also depends on that person's circumstance as well. Take Nina for example, and her legal woes. How could I let her all by herself? I had to help her out: I could just imagine the mental anguish she was going through. Come to think of it: I really believe that most reasonable ones just want someone nice to talk to and help them out from time to time, like a normal human being. On account that the world is filled with bastards(both of the female as well as the male version).

How many:
Not tellin'

Which types do I like:
By far, the ones I like the best are those who ask for advice (personal or professional), and those who try to educate themselves. They see this as an opportunity to learn from someone older and more experienced. I really enjoy their companionship because it shows they have a brain behind that pretty face, and by talking to them you can forge some kind of bond. For example, there was one who asked me how can she get out of debt. So we had a long discussion about that. After all, instant cash allowances, while nice and good, can only get you that far. Like I mentioned earlier, most SB's will just go ahead and spend it all on shoes anyway instead of investing it somewhere. Except maybe for an aspiring day trader I met once. I kind of laugh when I think about that one: Day trading? Gimme a break! Someone is going to get their butt handed to them...But that's OK: school of hard knocks.