You are asking a very difficult question here. In fact at this very point indeed classical electrodynamics breaks down. It asks nothing less then after the "self-energy" of the electron. In the classical picture usually one considers the electron to be a point particle. Let's consider one electron sitting at rest in the origin of the coordinate system. Its electric field is the Coulomb field (written in SI units),
$$\vec{E}(\vec{r})=-\frac{e \vec{r}}{4 \pi \epsilon_0 r^3}.$$
Now the very argument you bring in #1 shows that for
continuous charge distributions at rest the total energy of the electrostatic field is given by
$$\mathcal{E}=\frac{\epsilon_0}{2} \int_{\mathbb{R}^3} \mathrm{d}^3 r \vec{E}^2(\vec{r}),$$
i.e., the electric field's energy density is
$$u(\vec{r})=\frac{\epsilon_0}{2} \vec{E}^2(\vec{r}).$$
But now comes the trouble, if you want to apply this equation to the case of a pointlike electron! Plugging in the Coulomb field gives the energy density
$$u(\vec{r})=\frac{e^2}{32 \pi \epsilon_0 r^4}.$$
This is highly singular at the origin, i.e., the location where the point charge sits. To regularize it we have to integrate over all space taking out a little sphere of radius ##a##. Then using spherical coordinates, we get
$$\mathcal{E}_{a}=\frac{e^2}{8 \pi \epsilon_0} \int_a^{\infty} \mathrm{d} r \frac{1}{r^2} = \frac{e^2}{8 \pi \epsilon_0 a}.$$
The total energy in the Coulomb field of a point charge thus indeed is
$$\mathcal{E}=\lim_{a \rightarrow \infty} \mathcal{E}_a =\infty.$$
The regularized energy would be correct, if we'd consider the electron as a spherical shell of radius ##a## carrying the electron's charge. So the assumption of a mathematical point charge leads to trouble in classical electrodynamics, and that already for the most simple static case!
In fact, the entire issue becomes even worse when considering a point charge moving in an arbitrary electromagnetic field: Then it's accelerates and radiates off electromagnetic radiation. This carries off energy from the particle's kinetic energy, which means it should be damped. Trying to take this into account for a strict point charge leads to an equation (the Lorentz-Abraham-Dirac equation) which gives rise to completely unphysical motions of the electron: Rather than simply radiating off some energy as e.m. waves and being damped the equation also leads to the prediction that the electron self-accelerates (i.e., out of nothing even without external fields the electron accelerates!) and there are actions from the future too (runaway solutions and preacceleration).
The solution within classical physics is to consider a classical particle of finite extension, i.e., not a point charge but something like a little charged sphere. One has to take into account some stresses to keep the charges together too. The equation of motion is, however, now not only a differential equation in time as is usual in mechanics (basically Newton's ##\vec{F}=m \ddot{\vec{x}}##) but a socalled differential-difference equation. There's a vast literature on the subject. A very nice pedagogical discussion of the model of a charged spherical shell as a model for an electron of finite spatial extent is
https://aapt.scitation.org/doi/abs/10.1119/1.3269900