Ady, Chris, thanks for the advice and the research. I really appreciate. This is very helpful. I will try to put in practice this weekend: Looks like we might have a few 11-14 knots moments.
Chris, you mentioned that you would be sailing a 8.5-ish in 13 knots wind. Sail-sizing for any given condition is really something I lost an appreciation for. I know it takes time and practice to get familiar estimating that kind of things. I played with the online sail/wind calculator a few days ago but everyone's experience and preferences are different. So, could both of you share with me what sail size you use in what kind of wind/water conditions? I know that skill level, weight, board and sail type, etc., are important factors, but sharing your personal experience on this topic would put things in context and hopefully help me to better estimate the size I should go for.
Many thanks.

It is very circumstantial but approximately it looks like that for my 170 lb. /the wind knots are the middle of the sail range/: ~15 kts-7.5; 20-6.5; 25-5.7 used on Atomiq 110 and then between 25 and 40 kts I use a 5.2;4.7 and 4.2 on a Kode 86 . On Lake Michigan where the wind is more intense and Im dealing with chop and swell the numbers are smaller usually.

I am most often sailing Lake Michigan on a 220L Exocet windsup (this is my most-often used board now, both for planing conditions and for catching small waves in winds as low as 10mph) or a 145L RRD Fireride. Depending on how much dessert I've had the night before, I'm somewhere between 175-180 lbs, and in MPH, here's my sail range: 13-15 mph = 9.5m, 15-18 mph = 8.5m, 18-20 mph = 7.0m. Over 20 mph, I'm inclined to switch to a 108L RRD Freewave: 20-24 mph = 6.0m, 24-26 mph = 5.2m. I also have a 94L FSW that I haven't tried yet, but which would work with the 5.2 sail or a 4.7 in 26-29 mph winds.

I should probably mention that I dearly miss ~95L board for the 6.0-5.0 wind range-which is the most fun range btw, but I'll get one first thing when I save the money. For your weight Greg this will be rather the~ 105 L size ,Chris is lucky to have his 108 L.

4th session yesterday. Lake Winnebago, WI. 15-18 knots gusting 25. Water in the 60s and air in the high 70s. Awesome!

Progress! I got the board to plane many times. Used a 6.5 and was perfect.

I'm starting to understand what Ady was talking about regarding body position to get into the back strap: it seems I need to get my hips parallel to the board to get my foot on the back straps this close to the rails. There is no way the foot can get in there while the hips are facing forward in a 7 position. The only back strap I can find in a slightly forward stance is the leeward back strap! This is a huge piece of info and discovery, because I couldn't understand why I couldn't get in the back strap as I had master foot straps for years in all conditions in a single and centered back strap config. This was a big revelation for me on the water yesterday! I still didn't succeed in strapping my back foot, but now I know why and can work my stance to get there. For anyone who never used one of those freeride or freerace board with back straps on the rails, understanding the change of posture one has to learn is quite critical.

I have to say that for me, riding parallel in a more 6- like posture, is very unnatural and scary. I haven't fully committed to it because I need to rely more on my harness to keep me stable than to rely on my front foot to generate an opposing force. But that will come.

Basically, on this type of board:
When off the straps the body forms a 7 with front leg extended forward and the hips facing towards the mast
When in the straps the hips are more parallel to the length of the board and the stance looks more like a 6 with the front leg a bit more flex and not as locked straight. Is that right?

There was about a 2-foot chop that day and the board is extreeeeemly fast when planning! (a LOT more than my old 80s board as I can recall). This was super-scary with no foot in a back strap and almost impossible to maintain more than a couple of hundred yards without being thrown in a pile along with the gear!

Last thing that seems to be more critical on this type of board than on a single central back strap board is timing: as soon as planning happens, it is imperative to put in the front foot. Then, the back foot has to follow pretty quickly behind to help stabilize and control the board in the chop. If the speed gets too fast and the back foot is still on the deck, there is almost no way I could put it in because the board becomes at that point too lively, bouncing on the chop and edging on the rails alternatively as I pass through the chop. On flat water, I'm assuming this wouldn't be such an issue though. But timing seems quit important in messy waters.

Overal this was a fun learning day until I stepped on stupid zebra mussels and cut my foot! That's what happens when you leave half of you brain along with the booties at home! Live and learn.

Oh yeah, you are getting there-fast!! Now some more TOW and overcoming the fear and all will come into place. Lets forget about the numerical description of the stance, beacause its getting a bit confusing. Ill describe it like that:
-atemting to plane and/or sailing downwind-bent, back leg, straight front leg , body is back
-sailing across the wind-both legs straight /the back one is a bit bent still a lot of time, but much less so compared to sailing downwind/ , body in central position between the foot straps leaning windward
- sailing upwind-straight back leg , bend front leg, body leaning forward
You are absolutely right that on a short board the faster you get done with the front foot the better, it equals stepping on the accelerator-the frontof the board lifts up free. At this point you have shifted your weight over your back foot /to be able to lift the front one and put it in the strap/ , to prevent rounding up push heavily on the boom! You start to accelerate fast now and the weight on your back foot increases at the same time. To lighten it up shift your body forwards while turning slightly upwind /it may help to lean the rig back at the same time /. Your weight will shift from your back leg to your front one and it will bent leaving your back one free to lift and get in the back strap.
This is the long version. With experience youll learn to do it all in one move when the wind is stronger. Now go out and practice

Did you move the footstraps?! Im experimenting with the front ones and I'll report about my experience soon.
Also have you checked for any crack-especially the nose area after all the crashing?

Hey Ady. Thx for the added details. Not too far away from success!
See pics for my current straps position. I didn't change them so far. Thoughts?
As far as crashes, they were not that bad and I managed to keep the mast away from the board. I just go with it for the ride!

Good looking nose and I was able to crack mine today. The spot was soft already /ex rental board/ so it was justa matter of time so I have some epoxy fixing to do. About the foot straps : mine actually has 3 rows if holes with 3 holes each and yours has only 2 rows, so you are maybe good for now exept that you may move them in the middle holes and eventually moving them to the outside row one day. I'm done experimenting and I've settled on the middle holes/ outside for both -front and back and today I was comfortable both upwind and downwind.

Cracks? That's unfortunate. Hope it's repairable.
What? 3 rows on the 2015 IQ? Now I'm jealous! I wish I could set in the middle. I would already be in the straps by now. ...Maybe. Ha!
Anyhow, I'll keep trying...
Thanks for all the advice and good luck with the repairs.

Now I can better understand the root of the problem. When you compare yours and mine stances in the pictures below you can clearly see the difference in the body position relative to board and rig. Its mainly down ti how the sails changed prompting a redesign of the boards along the way. While in the past the sails pulled forward and up requiring long boards that wont nose-dive and there was no need for much width or a big fin, todays sails pull more sideways and down /especially the bigger sizes/ which calls for more width and biger fin to be able to resist the pull and stop the board from sliding sideways and there is no more need for so much lenght anymore. Because of this developments our stance have shanged from being back and facing forward to being more centered and facing sideways. That old forward facing stance /although nit so much exagerated/ is only needed when sailing downwind /like when attempting to plane/ when you open the sail and make it pull more forward.
So Greag your next step after bearing away, making the board plane and putting your front foot in the strap is to start heading across and shifting your body position from facing forward to facing sideways and puting your back foot in the strap finally.

How funny would have it been if the model name of your sail above was "Futuristic"