Generalized hill climbing algorithms provide a framework to describe and analyze metaheuristics for addressing intractable discrete optimization problems. The performance of such algorithms can be assessed asymptotically, either through convergence results or by comparison to other algorithms. This paper presents necessary and sufficient convergence conditions for generalized hill climbing algorithms. These conditions are shown to be equivalent to necessary and sufficient convergence conditions for simulated annealing when the generalized hill climbing algorithm is restricted to simulated annealing. Performance measures are also introduced that permit generalized hill climbing algorithms to be compared using random restart local search. These results identify a solution landscape parameter based on the basins of attraction for local optima that determines whether simulated annealing or random restart local search is more effective in visiting a global optimum. The implications and limitations of these results are discussed.