Should I have my transcripts sent directly to the colleges I am applying to, or should I have them mailed to me? I'm worried that I will not receive them in enough time to mail them out.
At this point you won't have time to have them mailed to yourself unless you can go pick them up at the school. I had six transcripts so I had them all sent to me so I could make "packets" for the admissions people.
There is no penalty to have them sent directly to the schools. Only one school I know of (KSU) specifically states on their website that they prefer you package everything together and mail one packet to them.