I have several small pineapple plants growing too. First tried one the summer before last but it didn't survive last winter in my unheated sun room. This year I have seeveral more but they seem to be very cold sensitive. I took them in the same day (mid October ) as all my other tropicals (including citrus, bananas, small palms, dragon fruit, etc) And the biggest one especially showed cold weather damage already. I now have a 6' x 8' cheap green house set up inside my sun room with heat & lighting inside it. The pineapple plant is still alive but not happy at all. If they weren't free to grow (not having to purchase the plant I mean) I wouldn't bother again. But since its not costing me anything besides a little dirt and space I keep planting them.
Oh and for me the best way to get the to root was as previously posted. Twisting top off, let dry a couple days. Pull off about an inch or so of leaves from the bottom and then suspend over water not submerged a lot, just barely touching some water. Too far into the water and it gets mushy and rots. Then put in a sunny window and hope for the best. Change water regularly too.