Apparently Cannot Make My Own Decision. Want Your Opinion of Kid Furniture.

As long as the first one is a twin size bed or bigger I would go with that. I think you have good taste!

Personally, I'd probably go with a twin bed and a dresser. I think you'll find that the storage in the loft bed isn't going to work for very long. And I'd be afraid, at 2, that he would either fall out of bed or not be able to maneuver the steps.
I slept in a twin bed until well after I was in college. I think I was almost done with college before I got a bigger bed. But, I'm not a very big person either. Most guys I know don't like a twin bed after they hit puberty. They're all arms and legs! Makes sleeping in a twin hard. If you got the twin and a dresser, you could upgrade the bed later with out having to replace the whole unit. Normally, I'm not a fan of toddler beds, but if space is an issue, that might be something to consider.
As far as price, Ashley Furniture is on the expensive end of things. You should be able to find a nice twin bed at a better price than what is listed there. If you can, hold off until around tax time. Lots of furniture places have sales right around then. I know most of them also have President's Day Sales in February.

At this young age, cheaper is better, since over the years they will scratch/marker/peel veneer off of the furniture. So long as it is sturdy, I would get something off of craigslist or a cheaper furniture place (ikea even).

I like the loft idea, but I agree, I don't think it will grow with him very well.

I'd go cheap. We can afford something nice but I haven't gotten my girls much yet bc I figure they will want to pick something when they're older. Your son may really want something later. Our daughter's beds are just on the floor... Box spring and mattress. Who cares? They're little kids and not as high to fall off of.

I didnt look at your links but I think the best advice I can give when transitioning a toddler to a bed is to not get a toddler bed but to get a twin and use rail guards so they dont fall out. This way you can lay down with them and read stories and its a much smoother transition. We bought a simple twin bed at IKEA, Everything for under 100$.

If space is an issue, go with the loft bed. It looks like a twin size mattress...I slept on a twin mattress until I graduated HS. On the other had, my 10yr old daughter hates her twin, complains that it's too small (she is a restless sleeper and tosses and turns all night and has actually fallen off her bed), and desperately wants a bigger bed. So depending on how your son sleeps, this option could work for the next 15 years or for the next 7 - 8. But it's a nice looking piece of furniture, so style-wise, he won't outgrow it ever.

I prefer the look of bed #1 and the functionality of all those wonderful drawers which would be great for some toys as well as clothes. I just understand that the quality of the furniture is important too. How will this furniture hold up over time? If bed #1 is twin sized I would get it. I guess I would probably be looking for something that has a bunk or trundle for when he has sleep overs unless you plan on moving before he becomes old enough to have sleepovers in which case I may consider holding out until then for more sleeping options in his room.

Great tastes by the way.

You said he doesn't have a lot of room - but you don't know if he'll outgrow a twin bed when he's older....my suggestion would be to get him a twin bed (daybed or twin) with a trundle underneath.

I love Ashley Furniture (bought most of our furniture there) but when you said you don't want to spend a lot of money on kid furniture, I thought you meant Wal-Mart, not Ashley!!!

What I love about the twin/daybed with a trundle is that if he gets bigger, you could have him use both beds. If he gets bigger and doesn't want that for his bed, it's a great extra bed for overnight guests.

I like laying with my daughter on her twin mattress right now so the first would be out for me. The second one is on rolling wheels so I think that may be an issue (he may use it to roll around the room!).

So in that respect, I'd get the second one but ensure it has locks on the wheels or go without the wheels.

How about this:

http://www.ikea.com/us/en/catalog/products/10123996

We have it and LOVE it. It can be assebled with the bed on the bottom for now, or you could still assemble it with the bed on top and put another mattress on bottom for your little one to sleep until you are comfortable letting him sleep on top. And they make a super cool blue bed tent with white stars on it that goes on the top bunk, or over the open space at the top if you assemble it where there is only a bed on the bottom. The nice thing about it is that it is not as high as conventional loft or bunk beds (like at least a foot lower), so not as much danger factor. But it has the area underneath for play, or storage, or whatever. My son is almost 5, and we've had this bed for 2 years now. He used to have a mattress on bottom, but now we only have the mattress on top, with his little couch, and stuffed animals, and pillows underneath. It's his personal chill out space. :) The only thing we added, was a couple basic handles at the top of the ladder(screwed them right into the wood with no problem) so he had something to hold onto when climbing up or down the ladder.

I personally like the loft bed idea best because it's so useful. Have you tried looking on Craigslist for this item or similar bed combo? I know cutting costs is getting to be the #1 concern for American's now a days.....

That's what I would do - you have your mind set on a certain style...just keep looking for a little while longer (a couple more weeks) - unless you don't have the time and it's getting close to when you need the bed. Maybe look at stores that you would normally not look at too...they may surprise you with a hidden treasure. Even St. Vincent's or Goodwills. Good luck. But I really like the whole loft idea though.

I liked the first one better. Like you, I liked how everything was in one unit and you don't need to make space for anything else. Since he is just two he will use it for more years to come. What I would worry about with my two year old is that he would fall off of it, but he also rolls alot.

They both look nice. I think the first one is cute, but is it a twin? Is there a weight limit to it? I think it could be outgrown.....the first time I saw those stairs on a bed, they rocked my world. I thought that was the coolest thing ever! But I don't see a 10-12 year old loving it anymore, ya know?
One great great great option for storage (I'm talking STURDY, attractive, functional, the works) is the expedit system from IKEA. Go to ikea.com and search expedit and it'll pull up several different sizes. We have the one that is 69.99 and got attractive canvas crates of different colors from there to put in the cubes. Each cube stores different toys: train table accessories and trains, action figures, vehicles, music items, puzzles and art supplies, guns, blocks. It's pretty great! And it's solid wood, and can be stood up as a book case when he's older, or laid down on its side like it is now for the best toy system ever. He can take it with him to college, even. He's had it 2 years and no scratches yet. We sold 3 toyboxes on craigslist to go towards the money for this item. It saves space, keeps things clean and organized, and looks so much cooler.
My oldest is in a toddler racecar bed that I got off the DFW craigslist (it is sooo cute and he's loved it dearly)--I paid $75 for the bed, mattress, 2 sheet sets, and instead of just the little wooden slats the previous owners had cut the side of a metal crib (lots of little slats in one frame) for added support and comfort. That is a great deal! My youngest is in a portable crib that I got for my first child off the DFW craigslist (with mattress and 3 little fitted sheets and a bumper) for $40. I think at this age, craigslist (especially in the metroplex!) is so the way to go.
Since my youngest is about to get out of his crib and likes his big brother's car bed anyway, I've been discussing that with a new house, he should have a new room. How would he like to decorate? He wants a cowboy room (go figure) so we are saving to get him a bunkbed/loftbed (twin size) and just keep the ladder in the attic until we feel he's old enough for it (about 6?), and will redecorate his room a little bit. I've been searching on craigslist here but it's a smaller area so not a great choice of stuff......so we're just gonna be patient and wait for a big sale (President's Day? Memorial or Labor Day?) and purchase a loft bed with a built in desk, small dresser, and bookshelves.