Looking for experienced answer and putting Oye as tag, good to see, but not required. A lot of good people are there who can give you good replies.
Taking a virginity as it says in sex stories on blood and mess, with my experience of taking 5 cherries, I never seen that. The first time sex is always very cautious one, its a girl's biggest nightmare and its a man's responsibility to take care as slowly and skillfully as possible. If he makes a mistake, she will have a fear in her mind. If he does well, she will love having sex in future.
Answer to your questions:
1. The blood will come out when the hymen raptures. By use finger, tool or dick, it may rapture. Even by sports it may, like cycling, gymnastics, horse riding or similar. Meaning, she can lose so called virginity when she is still a virgin.
2. It depends. usually with skillful hand, not much. But its going to be more if her hymen is naturally thick in nature. Hymen can be thick or thin, tight or bit loose, it definitely will cause blood flow, but not like sex stories.
3. Safest is handle with care. Before inserting tool, take time, plenty of time. Do all the foreplay, including oral on her pussy. Get her extremely relaxed on mind and body. Go slow, very slow when penetrate. Do stop the moment she says to stop, and don't take out or go in. Let her be accustomed to the intruder. If you let her stay relaxed like hell, be sure she will love the act. Its a one time issue, has to be done as memorable as possible.
And for God's sake, don't get carried away by reading erotic stories, often they say give a hard push and keep fucking with lip lock so she cant scream, never do that. Once you are in, stay still inside for as long as she wants. Do make move once she says she is okay.
By the way, its always better to use some lube, in case you are unable to lube her hole. Try KY Jelly. Keep some tissue paper to wipe the blood.