I set a goal to do as much riding on my SS as possible this spring and eventually going all-out fixed by the summer. I currently ride a Windsor Tourist as my full-time commuter. Its a heavy hauler, geared low, etc. The first mile of my work commute is uphill. I will admit I could be in better shape, and could loose some weight myself. This being said, my one and only SS/FG is currently geared at 44/18T. Should I gear this a bit lower as I acclimate to SS riding? Or just tough it out and take my time on the hills? Or am I being unrealistic in what can be done with a SS/FG machine?

I welcome any comments or encouragement.

44/18 is about 65 gear inches...plenty low.
Just trying it once, you'll know soon enough whether it works for you.
Let us know how it goes.

When you get better at SS/FG riding, you spin faster, not bigger gears.

Start with a low gear at a moderate cadence. Try to spin slow enough to keep your HR from getting too high. When you get lighter and fitter, you'll spin that gear faster and keep your HR down.

44/18 sounds low enough. Have you tried your hill out yet? Maybe take a test ride one weekend to see how it feels.

Just do it.

Gird your loins if you are going to hang around this place.

I'm new to riding fixed and pretty new to riding in general. I'm in decent shape, but am not particularly strong or nothing. I ride 42/18 as there are a lot of hills around here. I'd love to have more top end, but with the wind and hills out here, 42/18 works for my chicken legs.

44/17 is the perfect gearing for commuting. Last year I was commuting with 42/17 which is similar to 44/18 and do just fine for my commute. Sure pushing big gears is cool amd all but it can get exhausting at times especially doing a 12-14hrs long shift. However I did gear up to 48/17 after doing my first road TT race but finished the season with 46/17. Like Carleton said, you get better at spinning faster and once you're there then you can start experimenting with different gearing but in the mean time just keep riding and eventually you'll get better.

No shame in getting off and pushing either, some hills demand no other approach. It's actually better physiologically to climb off before you explode and, rather than stop and gasp, to keep walking.

I have a stonkin' great hill on my commute and have managed to push my lactic thresh-hold quite a bit higher using this technique, mind you, I use a heart rate monitor and am enough of a nerd to read it and try to understand what it's telling me, you don't actually need one.

Find the combination closest to 65 GI on your Windsor Tourist, and practice going up that hill several times. That'll be your answer.

My guess is that 44/18 is plenty low for anything.

I have to ask, why are you riding single speed for a while before going to fixed?
If you eventually want to ride fixed, start riding fixed.

44/18 is a pretty low man, you'll be killing that hill after a week or 2. Mess around with a few different gear ratios and find what you like. That's a fun part of riding fixed, you can do it.

+1 dump the SS-- go FIXED; the learning curve is literally one ride... you learn really quickly that you cannot coast (make sure you keep the brakes)

I commute all year round and right now I am using platform pedals since I need to wear insulated hiking shoes to ride. Once the temps warm up, I can install my clipless and wear my cleats. That's why.

Good reason.

No reason at all. There is no need to restrict yourself to clipless, in fact, apart from periodic experiments that only ever support my preferences, clipless aren't needed at all. You DO need good foot retention for fg but all you need are good toe clips and straps. I ride the MKS Urbans with toe clips and straps, set firm but loose enough to get into and out of, and that's all that's needed. Beyond that, you need to think very carefully about your technique to gain any benefit.

Go fg now my son. Fit platforms, toe clips and straps, you'll be fine and still able to wear your funny shoes. My only advice is to clean and oil your geared bike first because if you don't, when you finally remember the thing in a year's time, it'll be rusty

This. It's just riding a bike.