I think not allowing players to save and reload whenever they want would be a huge mistake. People should be able to play their game however they want. For co-op, yeah I can see some rules being agreed upon by the group, but in single-player there is no justification for not allowing the player to play as they see fit.
For myself, I absolutely will reload my checks however many times it takes in one particular situation: any check involving an attempt to avoid combat and follow an alternate path around combat. Because I so dislike the combat system I will seek out any and all alternative paths to combat every single time. And if getting that alternative path involves a check roll, then yeah I will be reloading as often as it takes to pass that check.
