I'm feeling pretty stupid that I've spent some time on this and am still unsure of the answer, but it's been quite a while since I've done any trigonometry so if someone wouldn't mind explaining how to find a solution it would be very much appreciated!
The right-angled triangle, $\triangle ABC$, has coordinates, $A = (0,y_1)$, $B = (x_1,0)$, and $C = (0,0)$, where $x_1$ and $y_1$ are unknown positive values. The hypotenuse has length, $\overline{AB}$ = $5a$ (where the value of $a$ is arbitrary).
The line, $\overline{DE}$, runs perpendicular to $\overline{AB}$, with the point, $D$, lying $1/5$ of the way along $\overline{AB}$, and $E$ = $(0,0.141)$.
What are the two possible values of the length, $\overline{DE}$, and angle, $\angle ABC$?

Recognize that the right triangles ABC and AED are similar, we have
$$\frac {AE}{AD} = \frac{AB}{AC}$$
Substitute $AE = y_1-y_2$, $AC = y_1$ and $AD = \frac15AB = a$ into above ratio,
$$\frac{y_1-y_2}{a} = \frac{5a}{y_1}\implies y_1^2-y_2y_1-5a^2=0$$
Solve for $y_1$ in terms of known $a$ and $y_2$,
$$y_1 = \frac12 y_2 + \frac12\sqrt{y_2^2+20a^2}$$
Then, the length of AD can be calculated as,
$$ED^2= AE^2 - AD^2 = (y_1-y_2)^2-a^2 = \frac14(\sqrt{y_2^2+20a^2}-y_2)^2-a^2$$
or
$$ED = \left( 4a^2 +\frac12y_2^2-\frac12 y_2 \sqrt{y_2^2+20a^2}\right)^{1/2}$$
Also, the angle $\angle ABC$ is given by
$$\sin\angle ABC = \frac{AC}{AB} = \frac{y_1}{5a} =\frac1{10}\left(\frac{y_2}{a}+ \sqrt{\left(\frac{y_2}{a}\right)^2+20} \right)$$