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Heya Stumpy. Chillies self pollinate, though folks also do various things to "encourage" pollination such as tapping the flowers or stems, using a brush to tickle the flowers and so forth. I'm a sporadic stem tapper for my sins. 
As far as overwintering it is entirely possible (though needs to be indoors or somewhere equivalent as they hate frost) and can give a much better and earlier crop than growing from seed (which can be too slow for some varieties to get much of a crop in the same year as planting the seeds).
I have tried three things so far found on various internet sites (all of which involved picking my favourite, healthy looking plants and bringing them indoors before frosts to a nice light windowsill):
1. The first one was just leaving the plants pretty much as is apart from some moderate pruning to make them neater and the shape I wanted to start from. Watering was probably only every week or two (each time they dried out and even then not drenching them as I would have in Summer). Once they started producing flowers I started weak feeds every week or two and boosted these up gradually if fruit set until Spring arrived. Flower drop did occur more in Jan/Feb due to low light levels I think, I started tapping at this point!
2. With the second method I cut back the whole plant to around three or four inches above the ground so it was pretty much just a stem (few with tiny leaf clumps) and reduced watering to a very small amount every couple of weeks. Once the plants started growing back (around Feb/March for most of mine, a little earlier for the tiny leaf clump ones) I watered as necessary and started weak feeds until they were flowering and back to normal levels in Spring.
3. The third one I tried was cutting back the plant to around four inches of bare stem with rootball trimming to match (height of rootball four inches below the stem base) then replacing in fresh compost. Very minimal watering (every week or two, slightly damp only) until it started to grow back in Spring, then boosting water and feeding gradually until back to normal levels in Spring.
As far as I have noticed, the first method allows you to get chillies in Winter if light levels are right, but stresses the plant. With both methods one and two I ended up refreshing the compost with a quick spring repot to get the plants back to moderate health, as they ended up looking a bit sickly by the time Spring arrived. The advantage of the second method over the first was plant health for sure - the chillies did appreciate the rest and did better than their counterparts overall with total crop.
The third method is my preferred, though as two plants never grew back (I think due to overwatering while dormant as these two were accidentally watered too much while I was on holiday and got wet rather than damp roots) I would say it is riskier. The big advantage seemed to be plant health - the harvest from this method easily outstripped the other two.
Would definitely be interested in trying other methods though if anyone has any good knacks? I have more plants this year that I want to keep so am after something really reliable!
As far as overwintering it is entirely possible (though needs to be indoors or somewhere equivalent as they hate frost) and can give a much better and earlier crop than growing from seed (which can be too slow for some varieties to get much of a crop in the same year as planting the seeds).
I have tried three things so far found on various internet sites (all of which involved picking my favourite, healthy looking plants and bringing them indoors before frosts to a nice light windowsill):
1. The first one was just leaving the plants pretty much as is apart from some moderate pruning to make them neater and the shape I wanted to start from. Watering was probably only every week or two (each time they dried out and even then not drenching them as I would have in Summer). Once they started producing flowers I started weak feeds every week or two and boosted these up gradually if fruit set until Spring arrived. Flower drop did occur more in Jan/Feb due to low light levels I think, I started tapping at this point!
2. With the second method I cut back the whole plant to around three or four inches above the ground so it was pretty much just a stem (few with tiny leaf clumps) and reduced watering to a very small amount every couple of weeks. Once the plants started growing back (around Feb/March for most of mine, a little earlier for the tiny leaf clump ones) I watered as necessary and started weak feeds until they were flowering and back to normal levels in Spring.
3. The third one I tried was cutting back the plant to around four inches of bare stem with rootball trimming to match (height of rootball four inches below the stem base) then replacing in fresh compost. Very minimal watering (every week or two, slightly damp only) until it started to grow back in Spring, then boosting water and feeding gradually until back to normal levels in Spring.
As far as I have noticed, the first method allows you to get chillies in Winter if light levels are right, but stresses the plant. With both methods one and two I ended up refreshing the compost with a quick spring repot to get the plants back to moderate health, as they ended up looking a bit sickly by the time Spring arrived. The advantage of the second method over the first was plant health for sure - the chillies did appreciate the rest and did better than their counterparts overall with total crop.
The third method is my preferred, though as two plants never grew back (I think due to overwatering while dormant as these two were accidentally watered too much while I was on holiday and got wet rather than damp roots) I would say it is riskier. The big advantage seemed to be plant health - the harvest from this method easily outstripped the other two.
Would definitely be interested in trying other methods though if anyone has any good knacks? I have more plants this year that I want to keep so am after something really reliable!
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