LittleMiss I have heard similar stories all over the place, so you are not alone at all, sweetheart.
Luckily for you you are well off enough to do whatever you want, which is a real plus. I would suggest that something that might help you decide would be to find opportunities to get out and around others. Of course, I expect the Dakotas are not the best place for finding other girls like us. But with your resources there are plenty of options.
Major cities (LA, Vegas,Chicago etc) offer "makeover" services, where you can get professional assistance in learning how to maximize your assets. One of the best, apparently, is Phoebe Cross who is located near Atlanta. She is supposed to be brilliant at helping girls find the absolute best clothing style and wig shape and so on for those like us, and her services are reasonable. Her background is in hair and makeup for film but also with a lot of experience around TG people. She even allows you to stay at her bed and breakfast style farm while going through the makeover during your weekend there. And Atlanta is very TG friendly and Phoebe will even escort you on an outing to a local restaurant or club if you like, so you can experience being out with your new "look".
And then there are the various events that take place around the country. These are usually multi day events that take place in and around a major hotel in a TG friendly market, and draw girls from all over the country to an environment where they can be en femme for several days in a row, surrounded by resources and friendly faces, and a wide variety of opportunities to interact with others in different settings. All many of seminars are offered, from wig choice and makeup to HRT advice to voice feminization assistance and everything else you might want. And all of this is coupled with meals, dances, outings and formal events designed to give every possible growth opportunity.
One such is Keystone in Harrisburg, PA, unfortunately taking place next week I believe.
But another takes place in Atlanta in early September and is the largest in the country. By all accounts it is heaven. I plan to attend that one this year. It is called Southern Comfort. A quick google of that name coupled with "TG" and you will locate it. Hotel reservations are already open and convention registration begins on April 1. I believe Phoebe Cross is usually in residence there during the event and available throughout for consultations. There are others as well, of course.
My point is that it seems you have a pretty good idea of yourself, and resources to explore further. Why not see how it feels? The only way you will know, is to see how it feels to be yourself, en femme, in everyday situations. No one finds happiness in solitude. The closet of a home is still a closet. For some, that is the best option and the only option they have. I sense that is not the case for you. I get the feeling you are dying to "let the girl out". I can relate.
As to the wig, well, not much to do in that department, but I assure you that a properly fitted wig, in a style that suits your facial features and age bracket, can be very comfortable and also make a world of difference in how you feel about yourself. If it is a good one and well fitted, you quickly forget you are wearing it and it just becomes part of you.
One last suggestion.
This site is great for all the wonderful people here, and for the love and support, as well as for all the great knowledge and information available here. But in the greater sphere of the TG world, there are other sites that go way beyond the resources here. After all, we are a tiny corner of this world for those trying to grow breasts through herbs. Many TG people dispute the value of herbal HRT and thus shun this site (their loss!) But for other forms of support (hair, makeup, clothing, support with emotional issues, SO's, therapists etc) I suggest getting involved over at http://www.crossdressers.com (do NOT mention herbs there! very antagonistic response and even rules against it), or at Susan's Place http://www.susans.org.
On these sites you can see just how many more of us there are, make friends, and get a lot of information and support.
All of these resources are available. And you, honey, are in the exceptionally enviable position of being unencumbered by children, unsupportive spouse or lack of financial wherewithal. Many would kill to trade places with you...tee hee.
You may, upon gaining further experience and confidence, decide you want to go further. And you may discover it is not for you after all. But the best way to know is to explore, isn't it?
Oh, one little thing, LittleMiss... and I don't want to offend you, honey... but this site caters to bio males, but is essentially set up for gg's. Though none of us are "morality police" it might not be the best site for getting too much into kinky stuff. All our comments show up on the main board under "new postings" and are seen by a wide range of people. Eve, the administrator, is an absolute angel, and gives us free range to talk about whatever we like, but we don't want to abuse that. If you want to discuss "lifestyle issues" and I understand wanting to share that side of yourself, PM's to other members, or other sites more attuned to that (https://fetlife.com is one, I am told) are probably a better bet. Most all the members here are, at least to the best of my knowledge, pretty straight and mostly hetero. Again, just a gentle suggestion aimed at keeping everyone happy, ok?
Good luck, honey! It sounds like you are on a good path for yourself finally. We are glad you found your way here. Welcome home, sister!