New Year, New Training Plan

I've consistently been working out 4-5 days a week now for the past month or so, and I believe my body is getting used to additional workouts while tired. I've been on the bike trainer probably 5+ times this month, and actually set up the tri bike to get a feel for it, as well as the aero bars which I have never used before. The bike itself is fairly comfy, and the aero position definitely puts less pressure on the biggest part of my butt-bone, but I can't say that it's gonna be exactly "fun" cruising on that thing for 6-8 hours come October. My Orange Theory workouts continue, and I really feel like they've impacted my endurance and strength in a positive way. I typically do no more than 3 miles during any one workout with them, but today I was able to do an 8 miler with only a few walk breaks for water and up the last hill. I felt mostly good throughout, and having the company of veteran Ironmen (and women) helped since I was able to bend their ear about training tips, the race itself, etc. One thing that I believe I may have to change my mind about is the start of my training. The Muncie half IM is on July 10th, which places my first week of the 20-week training program on February 23rd. I'm being told this is way too early to train, especially since IMLOU isn't until October, and that I'm gonna be burnt out if I start that soon. One of my tri friends, Jeff (a 5x IM finisher) tells me that if I start at the beginning of May and increase my bike rides by 5 miles every weekend leading up to Muncie, then I should be fine (if that first ride starts at 30 miles). It definitely makes sense, and I know that I can do the half-marathon that follows because I've done approximately 24 already. Again, it's the bike that always concerns me. I've not been in the pool for nearly a month. At first it was because I had a terrible cold that lasted 1-2 weeks, and then it was the thought of stripping down and jumping into the water while the outside temp was 30 degree (yes, yes, the pool is INSIDE, but still. I'm a winter-wimp and I don't enjoy being cold at all). Mostly though, and this isn't an excuse, I really want to work with a coach for a few sessions on my swimming before I dive back in (pun intended) to ensure that I'm using the proper technique swimming at my best efficiency. Since the training isn't starting until late-February however, I don't see the sense of starting with the swim coach until the week prior to, or maybe even of, that first training week. And I can honestly say this is not procrastination talking - but more so I feel that it makes good sense to not be logging a bunch of "junk meters" in the pool if I'm not swimming correctly or efficiently. That's that. So, in summary, I'm still on the fence about when to start training. Perhaps I'll check the scheduled and incorporate the workouts on the schedule into my already-established workouts - just not stick to it verbatim or do daily or twice-a-day workouts that it sometimes calls for. Again, I want to make sure I am prepared for the "Big Dance," but I don't want to burn myself out either, and hate life come June.