This paper considers a variant of the Vehicle Routing Problem with Time Windows, with site dependencies, multiple depots and outsourcing costs. This problem is the basis for many technician routing problems. Having both site-dependency and time window constraints lresults in difficulties in finding feasible solutions and induces highly constrained instances. Matheuristics based on Mixed Integer Linear Programming compact formulations are firstly designed. Column Generation matheuristics are then described by using previous matheuristics and machine learning techniques to stabilize and speed up the convergence of the Column Generation algorithm. The computational experiments are analyzed on public instances with graduated difficulties in order to analyze the accuracy of algorithms for ensuring feasibility and the quality of solutions for weakly to highly constrained instances. The results emphasize the interest of the multiple types of hybridization between mathematical programming, machine learning and heuristics inside the Column Generation framework. This work offers perspectives for many extensions of technician routing problems.