Yes,you would need to cut thru the other estates otherwise you could end up going all the way round the houses to get to the other side if you understand what i mean.If you cut straight through the other estates that is and not head down the motorway
I doubt very much you will find any work in La linea,although it is practically opposite Gib,there are not many english speaking people working there,and the spanish people really dont speak much english there.
there are a few kite surfers and surfers along the beaches,but not many,only the odd few.much better surfing conditions in Tarifa.
scooters are the best way to get around,at the moment the spanish border guards have been striking for a pay rise,and the ques to get out of Gib have somedays been 3 hours,not what you need when you finish work .
If you are on a moto,you just push thru and can be out in 5 mins.so yes motos are the best option.Also free parking everywhere for them.Parking your car is difficult,there is a car park near la linea bus station which charges 1.50(euros)per day,but you have to be in there by 7.30- 8.00am otherwise you wont get parked.Yes the border is open constantly all day every day,so no worries about getting locked in Gib and not getting home!