I'm just wondering if there is a simple rule of thumb for it.
There is not.
If you have all the information the chip designer has, you can run a simulation to find an acceptable value. That's why we normally look to the datasheets for our chips (which are written by the companies that designed the chips and therefore have the necessary information) to tell us the appropriate decoupling capacitor.
7805 TO-220 from adafruit as that is what I am going to use it for
In the datasheet for the 7805 (TI version) it says this:

So the output capacitor is not required, but it will improve the transient response to add a 0.1 uF ceramic disc capacitor on the output.
Also if possible can you tell when to use a resistor paired with the capacitor
When the datasheet tells you to.
Assuming you're asking about output capacitors on linear regulators, this is sometimes required to maintain stability of the regulator. Newer chips (designed after 2005 or so) will tell you this is required in the datasheet.
For older chips (like the 7805) the datasheet may have been written before capacitors with low enough resistance to cause a problem were available. For those it's better to stick with relatively large capacitors such as were available when the chip was designed rather than use the smallest size SMT capacitor that is available today. So stick with 0603 size (EIA) for 1 uF or 0805 for 10 uF, or even use a THT capacitor as recommended in your 7805 datasheet.