We investigate the viability of observing charged Higgs bosons (H^+/-) produced in association with W bosons at the CERN Large Hadron Collider, using the leptonic decay H^+ -> tau^+ nu_tau and hadronic W-decay, within different scenarios of the Minimal Supersymmetric Standard Model (MSSM) with both real and complex parameters. Performing a parton level study we show how the irreducible Standard Model background from W+2 jets can be controlled by applying appropriate cuts and find that the size of a possible signal depends on the cuts needed to suppress QCD backgrounds and misidentifications. In the standard maximal mixing scenario of the MSSM we find a viable signal for large tan(beta) and intermediate H^+/- masses (~m_t) when using optimistic cuts whereas for more pessimistic ones we only find a viable signal for very large tan(beta) (>~50). We have also investigated a special class of MSSM scenarios with large mass-splittings among the heavy Higgs bosons where the cross-section can be resonantly enhanced by factors up to one hundred, with a strong dependence on the CP-violating phases. Even so we find that the signal after cuts remains small except for small masses (~< m_t) with optimistic cuts. Finally, in all the scenarios we have investigated we have only found small CP-asymmetries.