The current renewable-driven generation expansion wave, pushed by high renewable targets, is not accompanied by the same movement in the transmission expansion planning (TEP) side. In this context, new techniques are needed to balance the cost of relying in expensive reserve resources and the cost of building new lines to ensure least-cost reserve deliverability and foster new renewable projects. The situation is worsened in the presence of contingencies, where the interaction between the optimal reserve siting and deployment, the amount of renewable curtailment, the construction of new lines, and the selection of candidate renewable sites to be developed became even more complex. This paper presents a two-stage min-max-min model for co-optimizing the expansion of the transmission system and renewable generation capacity to meet renewable targets under high security standards and renewable uncertainty. In order to account for realistic reserve needs and its interaction with the expansion plan, correlations between renewables injection as well as generation and transmission (GT) outages are accounted for in a robust fashion. In order to ensure security within a flexible framework, the concept of compound GT $n-K$ security criteria is presented. Three case studies are proposed to illustrate the applicability of the proposed model. A case study with realistic data from the Chilean system is presented and solutions obtained with different levels of security are tested against a set of 10 000 simulated scenarios of renewable injections and system component outages.