how to make the opening sequence of (hero wanted )

[djgvinny]

i would like to do an opening sequence almost like hero wanted of cuba gooding ... where im walking with the personne in the street with the steadicam . the camera go up with the jib into the window inside the house . i have some ideas but required lot of matching frames aand i would like to know what s the best easy way to do it , if theres any tutorial would be good
thanks