BMR/TDEE questions

I've been looking at TDEE and BMR calculators recently and depending on the site my BMR is between 1669 and 1729. I'm 5'5, 29, and roughly 208 lbs. I have my calorie goal on MFP set at 1500. I checked my calories over the past few months and I only went over that in net calories 3 times (twice was barely over and I had one huge overage one day). Most days my gross calorie intake is between 1400 and 1800. I've been exercising regularly (5-6 days a week).

Calculating TDEE for light exercise 1-3 days a week (or one site just says exercise 3 days) I get a TDEE between 2298 and 2377 depending on the site. So my question is, should I always be eating at lease the calories indicated by my BMR and under the calories indicated by my TDEE? So for me, somewhere between 1669 and 2377? And of course, since TDEE factors in exercise I would base this off of gross calories not net calories so I would not eat back my exercise calories. My TDEE seems really high to me and I have a hard time thinking I'll ever lose weight if I eat 1800-2000 calories a day. And, if I calculate my TDEE based on moderate activity 3-5 days a week it equals 2664 calories.

Any advise would be appreciated. I think I'm over-thinking things but I'm sick of the weight roller coaster caused by eating too few calories then when I can't take it anymore I eat WAY too many calories and undo all my progress (and then some). I'm really trying to figure out how to be healthy AND lose weight.