Rashbak, my concern is not with the amount of dates or any other protocol issues you mentioned. My concern is with an aspect of chareidi shidduchim that many people prefer not to discuss or take into consideration. In my experience this is just how things are, but I may be ducking some virtual rotten tomatoes if anyone bothers to read this. I suggest that you do, Rashbak. Let me explain:
Although chareidim do allow the parties to meet and see each other, and as a result there is an element of considering whether they find each other attractive or feel comfortable with one another’s personalities, there is much more of an element of mekach u’mimkar- more of a business deal if you like. Guys and girls are graded (by shadchanim and by society in general) based on their family’s social standing, wealth, yichus, and also based on their own achievements in yeshiva/seminary, their appearance and popularity. Physical traits, intelligence, personality will move them up or down the shadchan’s desirability scale, but their family will also have a big influence on what shidduchim they’re being redt. Even a sibling who is divorced or ill will move them down a few notches.
Your relative comes into this at a disadvantage due to his coming from a “different” type of family. Even if he himself is an outstanding Masmid and a great guy, he’s not coming to this from the top of the ladder. You have to wonder if the girl has any disadvantages (she probably does) and what the nature of those disadvantages is. If she’s from a similar background, that’s your best picture. If she’s from a solid chareidi family, I would suggest you try to do a bit of inquiring to determine whether she has any issues that may have made her less suitable for someone from a mainstream “chashuv” chareidi family like her own.
Mazel Tov, and hope all goes well!