Winlink gets you closer, but as Don said it's not gmail. If your ARES (or similar) team drills on the FEMA ICS stuff, you likely have practiced sending incident and status reports this way.
The software (RMS express) actually has some canned templates and you can make more. Basically this allows the actual email message to only contain plain text, but the display formatting (think HTML) remains on the client side.
Suppose you want to send a status report to command. You'd fire up RMS express, compose a new message and select a form (template).
That actually launches a local webpage in your browser. You fill in the form like a normal web page and then submit it.
After submitting, you'll notice the body of the winlink draft email is populated using the VALUES you entered in the form. There's no tables, colors, or anything fancy.
But notice how there's an XML file attached. That is the style formatting that is used to display the data in a pretty format for upper management/brass.
When command receives this message, they locally use that attached XML with the email body contents to render the pretty report.
From a payload perspective, this is MUCH lighter than generating a PDF and attempting to transfer that. Remember, on a good day we're moving at 1200 baud. This is 1985 state of the art data transfer, but over RF.
That's the most common case, but I can also attach "normal" files, but be cautious of size.
Referring to this site:
http://www.ashep.com/sw/data-xfer-speed.html@ 1200 baud, it would theoretically take 6,990 seconds, or nearly 2 hours to send a 1 MB file. That's right - more than 2 hours to transfer a 3.5" floppy disc from 1995.9600 baud VHF packet is a thing, but not all radios can support it (well) and it may require some more specialized sound card interface/TNC. I understand even the popular TigerTronics USB signalink lacks TX/RX switching speed that can reliably support 9600. (rumor is a new product will be released this summer, but I digress).
But even if you and the other station both had 9600 supported hardware, you're still waiting 873 seconds for 1 MB. Okay, now we're down to 14 minutes or so. Maybe you kick off the transfer and go make a sandwich. That also assumes your connection is solid and won't get interrupted. RF packet links are relatively flakey, and often resending of packets is a common thing. This is a long way of saying you'll likely be SLOWER than 1200 or 9600 in the real world.
So these practical limitations are a big reason there aren't more tools to solve your problem.
