As has been stated 9 million times (or at least it feels like it), if you get the overstay permission you are then legally in the country. Although Migracion has never (we believe) deported a gringo for overstaying on the tourist card, technically they could do as there is nothing in immigration law which legally entitles someone to overstay.
The reason I would always get the overstay permission is because if anything happened to me - and serious things have happened to me in the past in this country - then I wouldn't want anyone to have the chance to say I am illegally in the country. I have two different travel insurance policies for the same reason, just to make sure I'm covered if the worst should happen.
You only need to look at the number of Haitians they are now deporting, literally rounding them up and sticking them on buses in the capital, and the hardening of attitudes to Venezuelans to realise that things are changing. Obviously rich expats are not the focus, but it wouldn't be hard to get caught in the crossfire on this one.