Child's Table and First Haircut: Your Advice?

I'm looking for a bit of future-predicting and infallible advice from my readers here. (Or if you find that impossible, just your general thoughts which may or may not apply to me.)

First, we're thinking of getting a child's table and chairs for Squeakles, like this $24.99 set from Ikea. We started thinking about it recently because we had a big box (that his toddler car seat came in) out in the living room for about a week and he absolutely loved driving his toy truck along the top of the box. However, we didn't want to leave the box in the middle of the room forever (now it's in his room, holding the car seat until the next time we rent a car), but we felt a little bad taking it away since he enjoyed using the surface so much. (Of course, he also enjoyed tearing off the mailing label and layers of the cardboard.)

But J isn't convinced that Squeakles would use the table/chairs, and actually neither am I. I think it would be nice if he used it to play with play dough, or maybe to sit and draw - but is that totally unrealistic?

Do your kids have a table like this and do they use it? And if so, do these same children spend a lot of time doing things like vrooming cars around, tossing Legos in and out of a container, dropping toys over the edge of the play yard, and running around in circles? Do they ever sit still? (Actually, Squeakles does sit still. He often puts his back up against the play yard while he plays with something in front of him or looks through a book.)

Second question, I think I'm going to give Squeakles a hair cut. Am I crazy?

I thought about bringing him somewhere to have his hair cut so I could watch what they do, but actually I'm a little concerned that they might cut it shorter than I want (even if I tell them not to). But if I do it myself, is it going to look horrible? Basically I want to leave some length, but trim off the parts that stick out from his head.

The long ends of his hair curl, and under the right conditions and viewed from the right angle, the curls look very cute.

But sometimes it doesn't curl up, and so it just looks weirdly fluffy over his ears.

Or worse, most of the time it looks ratty like this.

So even though I'd sort of like to keep the curls, I don't know if it's worth it since 90% of the time he looks more like he does in the last two pictures.

I don't want to go too short though. I think mainly I just want to trim the hair that falls over his ears and at the nape of his neck. But I don't think I will touch the top at all.

I've looked for general advice about cutting kids' hair and what I found were a lot of websites describing how to keep kids occupied so they'll actually sit still. Most said you should sit the kids in front of a DVD, but one person had the idea of just cutting their hair in the tub. I think I'll probably put Squeakles in the high chair in front of Yo Gabba Gabba. While the tub sounds like a good idea at first, I'll bet the reality would be a squirming slippery and curious baby.

What I was really looking for, though, was advice about cutting boys' hair in general since I have no idea how to shape it and really don't want it to have horribly straight edges because I don't know how to cut on an angle. I found this video online which seems like it will be very helpful, and has given me a little confidence.

But what's your experience? Are home haircuts hard to do?