Yes, they are quite different; size, gain, and radiation pattern.
A folded 5/8 is about 7' and has no ground radials. Ground radials effect impedance and pattern. At 50 feet, you might shoot the bulk of your signal right over the city and into the hills. There are a multitude of factors and you have to balance them out.
Look at the terrain and work backwards. Its not always about distance. You may want to focus on penetration where most listeners will be.
Look up pictures of radiation patterns for the antennas and decide what you need. I've used 1/4 wave groundplane in hilly terrain, 1/4 wave dipole in a tree on a hill side, a 5 element beam with a rotator for a long narrow city, a 5/8 loop for a house on a hill in the middle of a valley, and on and on. It depends on the goal and the terrain.
Don't forget to match the impedance to your TX.
You're looking at antennas capable of 300 watts. If you run 300 W into a wet string, you'll get plenty of coverage.