Measuring - good or bad?

My goal in gaining weight is to get to the weight range I belong in after having been in this "not low enough for others to worry but still far too controlled by the ed mentality" mode.  My weight right now is 100 at 5'4 - I think a good range for me is 110-115 (someone please correct me if I'm wrong on that).  I not only want to gain the weight but want to really be rid of the ed behaviors that go along with the controlling aspect of the ed. 

Measuring is a huge issue: on one hand my mind says to measure to ensure I'm getting enough in order to gain, on the other hand measuring to me can be a very ED minded behavior.  So which do you think is the right mindset to have?

Also, I really didn't want to be on a meal plan per se.  I wanted to get a basic calorie level I should eat at and just go by that.  In your experiences, is it better to have a meal plan (so many breads, proteins, fats, fruits/veggies, dairy each day) or have just a calorie total in mind?  Oh, and what calorie level would be best for me to be at to gain to a healthy weight?

Sorry for the flood of questions.

Thanks!

My problem is not undereating but overeating so when I don't measure I am unaware of how much I am eating.

Can you gain weight without measuring.... are you aware that you are eating too little?   Can you just conciously add more caloric but healthy foods to your diet like avocados and nuts and olive oils?  Watch yourself... be aware of what is working for you?  Evaluate .... then modify if it is not working. 

That's a good question.  I usually measure because I tend to overestimate the number of calories that I eat.  But if you think you have a good idea of portion sizes, it's probably a lot better not to measure and just pour some cereal into the bowl so that the obsession doesn't take over.  Maybe at the end of the day have an extra snack just in case you underestimated (something 100 or so calories).  I think I'm going to try to stop measuring soon, but I honestly think I would pour like 1/2 a cup and think it's a cup, so I don't know.

To gain weight you need to eat 500 calories above your burn for the day.  So say you burn 1800 calories in a day, eat 2300 and that will make you gain a pound a week.  I think your goal sounds good for now, you can always gain more if you feel like you need to when you get there!  Good luck!