Not so new, but here I am. Looking for advice/guidance

So, I'm not exactly new to My Fitness Pal, but this is my first foray into the community forums, mainly because the internet can be a scary place sometimes, especially for an overweight female. I've used MFP off and on for a few years now, but recently picked it up again and am determined to stick with it this time.

As a little background, I am currently weighing in at 214 pounds, about 30 pounds lighter than I was a few years ago. My highest recorded weight was 243 pounds. I suspect that I had been over 250 before I began to actually do something about it, though for the longest time I didn't even own a scale, simply because I just didn't really want to know the number. Like many people, I am battling the culmination of a lifetime of a poor diet and lack of exercise. At first, I took control simply through a diet change, eating healthier foods, cooking at home, and attempting portion control. The changes began to work. I did enroll in a formal weight loss program (VTrim, through the University of VT) and learned some healthy habits, also unlearning some not so healthy habits). I picked up My Fitness Pal the first time when I finished VTrim.

Since then, I spent about a year not really tracking my weight or thinking about dieting. I still continued to eat relatively healthy, but my portions were creeping up and my exercise dwindled to non-existent. So, here I am again. Let's do this!

My short term goal is get below 200 pounds. My long term goal is to get my BMI into the healthy range. I am currently considered morbidly obese (I am 5'6" and female). 150 pounds would put me at the high end of normal weight. Yes, I am aware that BMI is a flawed system, but it is a common indicator, and just once, I would like to be considered a healthy weight. At this point, I am not entirely sure if 150 lbs is doable, but I would like to try. I have a fairly large frame, complete with very broad, linebacker type shoulders. Nothing about me is petite or dainty.

I am trying to do this in a way that is healthy and sustainable, which leads me to the good old fashioned eat-less-move-more diet. I cook dinner for myself and my husband almost every night. I really enjoy cooking. Mainly I use Cooking Light for my inspiration, but I have a smattering of other recipes (and sometimes come across stuff on the internet that looks awesome and I have to try it!). For the most part, I measure my portions. I have a digital food scale that I use at home. If I eat on the road, I usually just eyeball the portion and make my best guess. My exercise so far consists mainly of walking. I walk to and from work most days, about 2 miles each way. I try to get at least a small walk in on the weekend as well.

My diary is public, and I would appreciate any feedback. Like I said, my goal is to lose weight in a healthy and sustainable way. I understand that this is going to be a long journey.

That was a long introduction, and now I have a few questions for those of you who have been at this a while.

How often should I be weighing myself? I am fairly obsessive and don't want o go overboard here. I generally weigh myself every day, and have taken to recording my weight once a week. Sometimes I weigh myself more than once a day and marvel at how much my weight can fluctuate during the day. Is there a preferred time of day to weigh yourself, or should I just try to be consistent with my "official" weigh ins? Also, when you weigh yourself, do you do it fully clothed, or do you do it wearing as little as possible?

Does the feeling of obsessiveness over the numbers ever go away? I haven't taken to doing my own spreadsheets (yet), but I have taken to meal planning a week in advance and plugging those meals into MFP. It takes up a significant portion of my free time. I don't want this to take over my entire life, and I really can't see being this obsessive about my caloric intake as sustainable long term.

I will be honest. I do not like exercising. I am glad when I do exercise and I'm also happy I did, but I will never like exercising more than, say, sitting on the couch, watching cartoons, and eating ice cream. I know this. I've started walking because it is free, easy to do, requires no special equipment, and can be done just about anywhere. I walk about 4 miles a day during the work week. Sometimes on the weekend I don't go for a walk at all, calling it a "rest day". Am I just making up an excuse to not exercise?

Thank you all for your support

-PiSquared