The DC collector current is determined by \$R_E\$:
\$I_C = \alpha \dfrac{9.4V}{R_E} \approx \dfrac{9.4V}{R_E}\$
Since you require \$I_C < 1.25mA \$, the constraint equation is:
\$R_E > \dfrac{9.4V}{1.25mA} = 7.52k\Omega\$
The second requirement, maximum output voltage swing, without any other constraint, doesn't fix the collector resistor value.
We have:
\$ V_{o_{max}} = 19.8V - I_C(R_C + R_E)\$
But, the voltage across \$R_E\$ is fixed at 9.4V so:
\$V_{o_{max}} = 10.4V - I_C R_C\$
\$V_{o_{min}} = -I_C * R_C||R_L\$
If you stare at this a bit, you'll see that maximum output voltage swing is 10.4V but this requires that the product \$I_C R_C = 0\$* which is absurd.
Now, if we also require symmetric clipping, then, by inspection:
(1) \$V_{o_{max}} - V_{o_{min}} = 2 I_C (R_C||R_L)\$
(2) \$10.4V = I_C(R_C + R_C||R_L) \$
Looking at (1), note that, for maximum swing, we get more "bang for the buck" by increasing \$I_C \$ rather than \$R_C \$.
Since we have an upper limit on \$I_C\$, (2) becomes:
\$R_C + R_C||R_L = \dfrac{10.4V}{1.25mA} = 8.32k \Omega\$
which can be solved for \$R_C\$.
*unless \$R_L\$ is an open circuit
One reason is that the transistor gain is degraded at high frequencies. To pick a specific example, the ON semiconductor BC546 has a gain-bandwidth product (GBP) of 100MHz at 1mA collector current (see figure 6 in the linked datasheet). This means that at a frequency of 27MHz, the current gain (beta) is about 100MHz/27MHz = 3.7, not 100.
At 27MHz, stray capacitances in the transistor (amplified by the Miller effect) may well also be playing a role in reducing the gain.
Simply replacing the transistor with one more suited to high frequencies may be sufficient to fix the problem. You may get away with just choosing a different general-purpose transistor: the 2N3904, for example, is a little better with a typical GBP of 300MHz. A better solution is probably to choose one of the many transistors designed for high frequency applications. To pick one at random, the PN5179 from Fairchild has a typical GBP of 2000MHz.
Because of the Miller effect, the common collector amplifier is not especially well suited for high frequency amplification, and topologies such as the common base amplifier are often used for signals at several tens or hundreds of MHz. However, at 27MHz I suspect you will be OK with a common emitter amplifier.
An additional factor limiting the gain is that the impedance of C4 || R6 needs to be added to r_e when calculating the emitter resistance at signal frequencies. Usually C4 is chosen to have negligible impedance at signal frequencies compared to the r_e of the transistor, but at 27MHz the impedance of your R6 || C4 is about 55Ω (dominated by the 59Ω impedance of C4). Switching C4 to a 1nF or 10nF capacitor should increase the gain by more than a factor of two.
Best Answer
There are several gains associated with voltage amplifiers. Consider the following model
In this model, the gain \$A_{VO} \$ is the open circuit voltage gain of the amplifier which, in your circuit, is given by \$R_C/r_e\$
But note that the output resistance of the amplifier (which is about \$R_C\$ in your circuit) forms a voltage divider with the load \$R_L\$.
So, the loaded voltage gain is:
\$A_{V} = A_{VO} \dfrac{R_L}{R_{out}+ R_L}\$
But, note that the input voltage \$V\$ is less than the source voltage due to the voltage division between the source resistance and the input resistance of your amplifier. Thus, the loaded gain with respect to the source is:
\$A_{VS} = A_V \dfrac{R_{in}}{R_S + R_{in}} = A_{VO} \dfrac{R_L}{R_{out}+ R_L} \dfrac{R_{in}}{R_S + R_{in}}\$
So, you cannot expect to measure anything close to the open circuit gain \$R_C/r_e \$