I have configured my SSL enpoint, and I can confirm that that is working. When I go into my log, I see the following:

Jul 13 08:14:10 support-dash app/web.1:  Express server listening on port 17621 
Jul 13 08:14:10 support-dash heroku/web.1:  Stopping all processes with SIGTERM 
Jul 13 08:14:11 support-dash heroku/web.1:  State changed from starting to up 
Jul 13 08:14:13 support-dash heroku/web.1:  Process exited with status 143 
Jul 13 08:15:48 support-dash heroku/router:  at=error code=H12 desc="Request timeout" method=GET path=/ host=app.supportdash.com fwd="68.63.87.85" dyno=web.1 connect=2ms service=30000ms status=503 bytes=0 
Jul 13 08:16:18 support-dash heroku/router:  at=error code=H12 desc="Request timeout" method=GET path=/favicon.ico host=app.supportdash.com fwd="68.63.87.85" dyno=web.1 connect=2ms service=30007ms status=503 bytes=0 

I tried to track down some information on exit code 143, and why all processes are being stopped. Check out the following server file:

var http = require('http');
var https = require('https');
var fs = require('fs');
var express = require("express");

var app = express();

app.set('port', process.env.PORT || 3000);
app.use(express.logger());

app.get('/', function(request, response) {
  response.send('Hello World 2!');
});

var privateKey = fs.readFileSync(__dirname + '/ssl/server.key').toString();
var certificate = fs.readFileSync(__dirname + '/ssl/gandiSSL.pem').toString();

var options = {
  key: privateKey,
  cert: certificate
};

https.createServer(options, app).listen(process.env.PORT, function () {
  console.log("Express server listening on port " + app.get('port'));
});

Thanks for your feedback in advance. I can provide more details if needed.

------ SOLUTION (EDIT) -------

See my answer below.

I found the answer here: Heroku Error H13 on ExpressJS Node HTTPS Server

"SSL termination occurs at Heroku's load balancers; they send your app plain (non-SSL) traffic, so your app should create a non-HTTPS server."

I then changed my file to:

var http = require('http');
var express = require("express");

var app = express();

app.set('port', process.env.PORT || 3000);
app.use(express.logger());

app.get('/', function(request, response) {
  console.log('[support dash] processing get request')
  response.send('Hello World 2!');
});

app.listen(process.env.PORT, function () {
  console.log('***** exp listening on port: ' + process.env.PORT);
});

Everything is working great no over https. Good Luck!