normally, car needs to be fully warmed up - both engine and tranny - before checking the fluid to get an accurate reading - and yes, it is checked with the car running and parked on flat ground. From the sounds of things, it has been seriously neglected... so i am going to guess the fluid is low. If you are loath to actually drive it, you can run it and just shift thru the gears without actually moving...
to get the dipstick loose, give it a slight twist.. they do like to seize in because they are not pulled as often as the engine oil dipstick.
also.. 4th gear will not kick in until the internals reach a certain temp.. if it is very cold outside it can take a bit to get things warmed up enough.