Eight days a week

My training experience says the following:
You can be pretty damn good at 3 sports.  4 is tough to fit in.  Pick the 3 that you like best (since I assume you aren't getting paid for this) and then set your schedule accordingly and then accept your good bad and ugly as your decision.  Swim, Bike, Run, Strength training in no particular order.

I've found that I can maintain the top 20% of sprint and olympic distance races and still do all 4 disciplines (but only lift 2x's a week) but the truth is I could excel in 3 if I dropped 1.  I've made my decision and plan on doing du's next season to see if I can better compete in my age group.  My disclaimer is that I have a wife, 2 children under 5 and a full time job in which I travel so time is limited but not an excuse.  I've lifted for 12 years now and just can't seem to stop from a vanity point of view even if it's no where near the 2 hours a day 6 days a week I did many moons ago.

Ditch the weight training if your goal is to get faster at triathlon. 

Fitting in two workouts a day is very acheivable and a fairly normal thing.  My training schedule has 13 workouts scheduled for this week.  I can't always hit every workout, but getting in 10-13 is not much of a problem and I have a very busy schedule(but no kids). 

There are a couple of things you left out.  First how big are you?  Losing weight in my opinion is free speed.  Second.  If you are very muscular (i.e. from strength training), then you should look at how much weight you carry from that.  I used to lift weights, and started this crazy sport carrying a lot of extra mass in my upper body.  That is not conducive to running or biking fast over distance.  Just saying. 

Finally, if you want to get faster, pick a discipline.  Work intensly on that sport for a month or two.  Maintaining the other two (say like 2x a week on the other sports).  Then switch.  It is easier to maintain speed then to gain speed.  Work out the kinks in swimming and get to your goal speed.  Then focus on say running for a couple of months.  Then biking. 

Also take a look at where you can gain the most speed.  Hammer that sport.  For me, cycling is easy.   But my swim sucks right now.  Make that your focus.

Just approach it one step at a time.  Don't try to change everything at once.  Good luck.

Doing the math, you spent 5min. in transitions.  You could probably cut that AT LEAST in half without ANY additional training, by just being smart(er).

Don't underestimate:

1.  Going from 50min. to 42min. on the bike.  That's a jump to 20mph. (at the dist. you cited).  That's no joke.

2.  Going faster, running, on training 3X/wk..

Good luck.

Transitions.  A lot of my 2.5 minute T1 was that I couldn't get my shirt on over my wet chest.  (I didn't swim with a wetsuit.) I've since bought a tri top to do the whole thing in.  That will help.

Bike: Going up to 20 mph, or 42 minutes for a 14 mile course,  on the bike:  Well, I went 16.7 mph sitting upright on my hybrid during the race.  I have since bought a tri bike.  I went out and did the same course, in about the same wind conditions, and did it in 46 minutes (18.25 mph), and that was without using the aero bars.  (At this point, I can't.  I need to learn to use them first, or else I will crash.)  So once I get used to the bike, I hope to get this up to 19.  Any increases after that will have to come from improving the engine, which, I know, is the hard part.  

Again everyone.  THANKS. 

Turn 2 runs a week into a brick workout.   If you have the time, this is how I am able to fit in the 3x3 a week theory.   That is without the strength training.   My schedule is maxed out with 12-13 hours a week so ironman contention may be out of picture, but find it just right for HIM plans allowing one to to be competitive.