For question 1 : It is only finitely additive, because if you have $A_1, A_2, .., A_n$ disjoint sets that have indicator functions $\chi_i$ that are Riemann-integrable, then you have $ w\left(\bigcup_{i=1}^n A_i\right) = \ell \left( \bigcup_{i=1}^n A_i \right) = \int_0^1 \sum_{i=1}^n \,\chi_i(t) \, dt = \sum_{i=1}^n \int_0^1 \chi_i(t) \, dt = \sum_{i=1}^n w(A_i) $ because the Riemann integral is linear. But if you take an infinite number of sets (say countable to start with), the permutation of the integral and the sum is not justified, because the move $ w\left(\bigcup_{i=1}^{\infty} A_i\right) = \ell \left( \bigcup_{i=1}^{\infty} A_i \right) = \int_0^1 \lim_{n \to \infty} \, \sum_{i=1}^n \,\chi_i(t) \, dt = \lim_{n \to \infty} \int_0^1\sum_{i=1}^n \chi_i(t) \, dt $ is generally justified by the fact that the sequence $\sum_{i=1}^n \chi_i(t)$ converges uniformly towards $\sum_{i=1}^{\infty} \chi_i$, and it clearly does not, thus we do not have proof. Note that if we use Lebesgue integration, this move is justified by the monotonic convergence theorem (or the dominated convergence theorem, because the $\chi_i$ are positive functions bounded by the $1$ function.).
For question 2 : You don't get the Lebesgue measure if you use the Riemann-integral to define $w$; take the indicator function of the rational numbers in $[0,1]$ as an example (the rational numbers in $[0,1]$ form indeed a Borel set) to see that you can't integrate every indicator function of any Borel set using Riemann. If you use the Lebesgue-integral to define $w$ then this is just trivial, because integrating $1$ over a measurable set just gives you its measure (this is partially how the Lebesgue integral is built, i.e. by taking functions that admit a finite number of output values).
For question 3 : I don't know if you can or cannot extend $\ell$ to a bigger set than the one of bounded functions, but the reason we don't know if we can is because we can't either prove there exists no extensions for $\ell$ at all, or because if there is an extension, we would prove there is using Hahn-Banach's theorem with a particular semi-norm that is majoring the Riemann integral. Note that this would be just one way to do it ; you can't prove things in a single manner only... although I'd be surprised to see something else come up.
EDIT : I think you might want to see this : since there are other generalizations of the Riemann integral, I thought they could be other choices for extensions of $\ell$ to different vector spaces. If you take a look at the Henstock-Kurzweil integral (let's say HK for short), I have never seen the proof of those results, but I remember reading on that page:
http://en.wikipedia.org/wiki/Henstock-Kurzweil_integral
that the space of HK integrable functions is bigger than the one of Lebesgue's functions because :
- If $f$ is bounded, then $f$ is Lebesgue-integrable iff it is HK-integrable.
- If $f$ is Riemann-integrable or Lebesgue-integrable, it is HK-integrable with the same value for the integral.
- $f$ is Lebesgue-integrable if and only if $f$ and $|f|$ are HK-integrable.
Now I don't know what being HK-integrable means, but I thought you could find out yourself and maybe build some interest for this integral if it suits your problem.
Hope that helps,