5 months enough training for first HI?

With your base, that's plenty if you're not after the podium.

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Agreed, with previous posters. 5 months should be plenty of time, and it sounds like you're starting from a decent baseline level.

When I'm asked "what's the best predictor for being able to finish strong in an 'XYZ' race" the normal answer is "the BEST predictor is having finished an 'XYZ' race before. In your case though, your experience riding 100 miles certainly bodes well for finishing 56 and running 18 likewise for running 13. As long as you can get comfortable in the water you should be fine.

The amount of time you have available is fine too -- if you can begin to squeeze out a bit more time on some weekends (especially between month 3 and 4) for a couple long rides and runs and bricks, you should be set up well.

You guys are good. I did leave out swimming as it sucks at the moment. I see this as needing to improve dramatically.

Anyone have any suggestions on a plan to follow or one of the memberships that are discounted at the moment?

My last sprint in August had a 800 swim that I think I did around 20-21 min. Around 3/4 of the way through I felt water logged and imagined if drowning is as peaceful as they say, it would have been a pleasure rather than finish. When I exit the water, I am think I am more exhausted than I should be, therefore not being able to put what I should into the bike and run.

Certainly no disrespect is intended to those that have perished during the swim portion.

You will be fine, but you do need to get regular swim practice in. Most plans will be fine, you should bump up the long run and long bike a bit more than most plans recommend (longest swim 2500, longest bike 65 miles, longest run 16 miles would set you up pretty).

Even if you cant afford a regular swim coach, try and get an evaluation session or two. Just one session with a coach that gave me a video and broke down swimming mechanics for me and pointed out all my errors did wonders for me...I'm still slow, but I can leave the water with energy for the rest of the race.

Will pursue a coach evaluation.

Hey, I could not swim 100m in one go when I started in August. After 3 weeks of swimming 2-3 times a week (30-45 minutes each time) I could do 2km comfortably! Not at world record pace but at roughly 2.40minutes/100m in a 50m pool, without getting winded/tired. Since then I have improved on the speed.
But I improved by watching some youtube clips about total immersion swimming. I was almost certain I could never do a triathlon in my life, maybe max a sprint due to my horrible swimming, but this really helped me amazingly.
Maybe it will help you too.

Search: "total immersion perpetual motion freestyle part 1" in youtube and watch parts 1 through 8.
At least it's free. Obviously if you have access to swimming coaches I am sure that might be better, but just wanted to share this as it did wonders for me!

I am also training for a HIM now, mine is in April and I am not in your condition so I must believe you can do this

If your swim is weak and this is your first HIM I would really focus on your swim fitness. This doesn't mean you need to be the first out of the water, it means that you want to have such deep fitness and confidence that when you get through the swim it feels like a normal workout. Having the confidence to tackle that is key and if done well will setup the rest of your day for success.

I just did my first HIM, had less than a year of swim training, and focused on it heavily but also kept everything else balanced as well. One of the best decisions I made in my training as my swim went extremely well (25 min swim but it was Augusta).