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Habanero Plant Diagnosis

I have a habanero plant that seems to be having some issues. It's just a Bonnie Plant that I picked up at Walmart a couple of weeks ago and transplanted into a container of Miracle Gro Organics Potting Soil. I gave it some 5-1-1 fish emulsion, some bone meal on the surface, and watered it really well when I transplanted it. I've been watering it twice per week since then.
 
I tried to pick the best looking plant that I could find but it did have some brown on the edges when I bought it. About ten days ago I looked at the underside of the leaves and noticed a small white spot with really small black specks on it. It may have been there since I bought it but I don't know. The leaf looked fine on the top at the time, but now there is a brown spot on the top side in the same location. I haven't found any other spots quite like that one with the black specks since then.
 
As time has gone on there have been a couple of the oldest leaves that turned yellow and then fell off. The first one had some whitish/yellowish spots on the top, the second one seemed more green around the veins. The thing that seems strange is that they would only turn yellow one at a time, I don't know if that is how it typically happens or not.
 
The other thing that concerns me is that all of the new leaves which have grown since I transplanted it have been a bit curled. There is also one leaf which has some brown spots more towards the middle which seem to be newer.
 
This is my first year gardening and all I know is what I've been able to find on the internet, so I'm a definite newbie. From what I've researched my guesses are that it is either bugs, or a calcium deficiency causing the leaves to curl. After looking at plant deficiency charts I'm unable to make a solid guess whether it's one of many deficiencies, bugs, or me just worrying too much causing the leaves to fall off. Any help would be appreciated. 
 

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Looks like you may be overwatering.
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Also...  Is there a good reason for adding the bonemeal?  If not, I'd skip that.  Doesn't do a bit of good in container plants, and it's a pathogen risk.  It can attract unwanted pests.  The fish fertilizer is great stuff, and will attract mammals.  But bone meal will attract critters and insects.
 
The white spot is most likely from some sort of pest.  But I wouldn't go messing with that unless you find out what they actually are.  It actually looks like it's isolated, so it's probably not an issue.
 
I cannot diagnose your specific problems, but I'd suggest worrying less. It's got new growth, it's alive. Pull off any pests, water it when it wilts, give it some fishstank once in a while, if you remember to. Next thing you know, you'll have a bunch of those crazy looking, zig zag shaped Habs that come from the strain that Bonnie sells. They're pretty good and definitely on the hot side.

Good luck
 
Update. I've backed off on the watering to once per week, but I may back off further since there is still moisture in the soil at finger depth.
 
The good news is that the plant has some flowers blooming on it. The bad news is that I definitely have a bug problem. I was gone on vacation for about 5 days and when I came back there were more of those whitish spots with black specks around them. They seem to be on all of the oldest leaves. I also found some black bugs stuck in some sort of silk that looks like spider webs. At first I thought that it might be spider mites (just guessing), but the bugs have wings and it looks like they are dead. I haven't been able to see any live bugs anywhere on the plant, but I have seen a few small bugs on the soil from time to time, but I don't know what they are.
 
In any case, all of the newer leaves are curled and seem to be struggling, though the pictures don't do it justice. I should also mention that I live in an apartment complex and the container is just sitting outside my door facing east, which means that the plant gets sunshine in the morning, but by 11:30 am it's in the shade for the rest of the day unless I move it out on to the grass for a few hours. How long does it take for a plant to recover from over watering?
 

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Well my plant is slowly dying. Those white spots with black specks are all over the underside of the leaves leaves. I had found some sort of bug crawling on the underside of leaves that are so small that I almost couldn't see them. They kind of looked like some kind of larvae but they are so small that I can't get a picture of them. I sprayed some neem oil on it but I think that it's too late; leaves are dropping left and right, it hasn't been putting out new leaves that I can tell and all of the ones that are left are the ones that are curled from over watering. I gave it some kelp meal today, but at this point I think that I'm just going to have to try again next year.
 
Yikes.  Chalk one up to defeatism...
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You're not even interested in staying the course, and learning lessons that might help you for next time? 
 
Well I'm planning keeping it and watering every week or week and a half, and fertilizing every few weeks as long as it's still alive. I'm just at my wit's end trying to figure out what it causing the problem. I can't find those kind of spots in any pictures on the internet. I just don't know what to do to help it.
 
You don't need to set a watering schedule, first off.  Water it when it actually needs it.  Secondly, if you get the pests under control, and don't manage to kill it by overwatering, you might be surprised at how well it rebounds.  Losing leaves during a pest infestation can come with a silver lining.
 
Leafhoppers. At least I'm pretty sure that's what it is; I found one on a nearby basil plant, a really little tan looking bug that jumped away like a cricket. Some how the habanero plant is still alive, but it's in bad shape as you can see from the picture. Any words of wisdom? Like I said above I used neem oil last week.
 

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