Usually they are re-potted during dormancy or in early spring.
If your VFT goes dormant or not in winter depends on where you live and more important where your plant lives .If you keep it inside all year long, it may not really go dormant just grow a bit more slowly. They are best kept outside and with colder temperatures they will automaticly go dormant at the end of the season.
If you only have one plant you can also put it in a ziplock bag and put it in the fridge during winter.(some people in warmer climates do it this way)
In theory the plant will keep going without dormancy but the growth will decline over the years.

You can self-pollinate a VFT and still get good seeds but it takes a loooooong time to get a grown plant(about 5 years,unless you grow the seedlings under light all year long)
What you can also do is take your flower stem(let it grow but don't let it flower) and then cut it in 1-2 inch pieces,then put the pieces upright in live sphagnum moss(make sure they're the right side up).After a while ,small plantlets will devellop at the underside of the stem and you can get new plants that way. If you have a plant you really like this is the way to go,because the plantlets from the stem will have the same propperties as the motherplant, If you grow plants from seeds(even if from a selfed plant) you never really know what kind of plant you will get.

Another tip is to grow them is deep pots, they do much better in them.