Hey Ashley, I understand your point with the fingering problems of extensions. But this can be trained, have you heard Edgar Meyer play his extension ? (I know it's terribly unfair to use Edgar as an example, please forgive)
Like I said before, I love 5 string basses more than anything but...
You already know that with a 5 string you usually have a better left hand performance in the low register, but a diminished right hand performance accross the whole register if the bass is poorly set up. The B string clearance is often an issue, or the clearance between strings. This is a big problem when there is no extra room to work with, like on smaller 5 string basses. These are not problems without a solution, but the solutions are usually expensive (neck, fingerboard, bridge alterations or replacements).You see, for you to be able to bow a fortissimo without hitting the adjacent strings, you need enough vertical and horizontal clearance between strings but.... The more clearance you give the strings between each other, the more you compromise the clearance with the C bout on both sides. It's a catch 22.
Sometimes the bridge alone gets replaced, to give more curve and horizontal clearance, and you end up with an unmatched bridge and fingerboard curve. This is actually a 5 string classic. Your end result is a very low string hight for the G and B strings and a very high one for the middle strings. Very unpleasant.
This clearance problem also means that you have less room for each string. It is a big problem when you need to play in thumb position. The G string is usually very far near the edge of the fingerboard, so the angle of your left hand and arm are not usually very comfortable at all, and your bowing angle for the G string is very restricted as well.
You will be amazed at how many very poorly set up 5 string basses you will find in Germany (the 5 string country par excellence). So your clean left hand work is not usually audible behind the constant rattling. The big orchestras like Berlin Phil don't have these issues obviously.
Do you need to play fast low notes? a five string might give you left hand ease, but the string is so thick that you very often loose definition within 10 feet. If you amplify you won't have this problem I think, but I am no expert in this field.
To be fair, when I decided to buy my 5 string, everyone advised me against it, and I am glad I didn't listen. So I think if your gut says that you're a 5 string man, then go for it.
Thanks for your vote of confidence Ken Smith.