"Since I started Paleo (or Primal really) I eat eggs almost everyday in the form of quiche. Whole eggs, not whites. I was wondering if that's what raised my total cholesterol. My quiche has eggs, lots of veggies, butter and usually some kind of meat (chicken sausage usually, but sometimes grass-fed ground beef or even shrimp)"
This is one of the many potential pitfalls of a modern attempt at a paleo diet. Some can get away with a diet high in cholesterol and saturated fats, but some may not. The problem is not the cholesterol, as this was likely high in a traditional paleo diet, but the combo of high cholesterol AND saturated fats is what can cause elevated cholesterol, as can elevated insulin/blood sugar. So maybe try ditching the butter (not paleo by any stretch of the imagination) and substituting sausage and beef for wild game or cold water seafood.
There can be so many reasons for low vitamin D levels that it is hard to work out what is wrong. Obviously sunshine is the best option, but the old recommendation of 10-15 minutes per day on hands and face is pretty far off the mark. That amount was based on someone who is fair skinned, at midday on the longest day of the year, and assumes an absolutely clear sky with no pollution or much water vapour in the air. Depending on where you live and your skin colour, you will need either a longer exposure or more body surface exposed. This is especially true if you are more than a month either side of the longest day of the year, or darker skinned. I would suggest hands and face are the worst things to expose, as these already get high exposure and are thus most prone to signs of aging, but that comes down to personal preference. We also become less efficient at making vitamin D from sunshine as we get older, so increase times again if you are over ~40. Even so, most of us store a great amount of vitamin D in our fat stores, and losing weight releases some of this most of the time. However, if you have been deficient for a long time, then you may not have much stored in fat. Alternatively, you may have not lost enough fat. You can count on 10-15lbs of weight loss from changes in fluid alone by switching from a high carb to low carb diet. This usually happens in the first two weeks. The rest of your weight loss may have been a combo of fat and muscle, so maybe your fatloss hasn't been as much as needed to restore vitamin D levels. Our ancestors counted on this fatloss over the winter months to keep vitamin D levels high enough for good health. Us modern humans don't undergo these seasonal fluctuations in fat gain/loss, and often miss out on crucial circulating vitamin D. Fat folks, even though they have the greatest stores of vitamin D, are often most at risk for low levels of circulating D.
Supplements usually work, but there are some reasons why they can fail. Not taking them with a large fatty meal is the main one, but many drugs also interfere with absorption. These include some very common drugs given to middle-aged and elderly people such as statins and antacids. Hopefully your doctor is aware of what drugs you are taking and their possible interaction with D absorption, but it never hurts to take your health into your own hands and be informed.
Hope things improve whatever you do!