I have had success and failure using both approaches. I have found that measured engagement works best for me. I just have fun with it, neg her and challenge her. I just don't send boring stuff just to keep a conversation going. If I feel it dying or want to leave her at I high spot, I just sign off. Many times, I have hit the send button thinking what I said was a little over the top, but F it. Except for a rare exception, the girls run with it. How many do you think get a hundred messages of "how is your day" or "You are really cute"? ZZZZZZ
A recent starter (she initiated after a tinder match)
Her: Where did you come from?
Me: My momma always told me that I came from her belly. You?
Her: I have been here the whole time
Me: There really isn't an option to leave and come back. That is unless you believe in that sort of thing.
Her: In a past life I think that I was a warrior princess. What would you have been?
Me: A general with his eyes on the throne.
Her: Ahh a king in the making. You would need a queen.
Me: Yes and that choice is a difficult one. A combination of smart and sexy. Know anyone?
Her: I might. So, Mr mystery, tell me something about yourself.
Me: I just did. Pay attention!
Her: Haha.. I am!
Me: Nice chatting with you. I have to run to a meeting. Talk later.
Her: OK TTYL
A lot of guys would have responded with a long message introducing themselves and actually telling her where they came from bla bla bla.
I sent her a few messages the next day and got her number. From there, it was about a week of scattered groups of texts, with a bit of innuendo that she picked up on (some are clueless or act that way) and built on. I do believe that f*cking their mind first makes many doors easier to open later by establishing at least some level of connection. The first date then feels more like the second. Some on here just go right for the meet. I wish that worked for me. As far as time goes, you have to feel it out and if I am busy, I can keep things warm until I get free time to ask her to meet. If I get shot down for a meet and she is still very responsive and she seems fun, I'll just act like it never happened and ask again when it feels right. I just back way off to see if I she seems to start chasing. Obviously, having others going is never a bad idea. At this point I can usually tell in just a few texts if things are going to progress. Some are just boring or dumb and some just don't get my brand of humor. That's fine with me.
Anyway, I ended up meeting the woman from the example for drinks and went back to her place to sample a wine that she had. Never even opened the bottle.
But I tend to be the type of person who is an old believer. In my opinion, there is no substitute for live communication. Many guys lying on the couch say what they are ****ing awesome, etc. But I believe that it is necessary to prove actions. To get to know a person, I choose a couple of questions from here 
