Hello furtivegain! and Welcome!
No, I won't yell at you. We all are perplexed by our appearances in some capacity. Some have more to question than others, yet the only way to understand these things is to do research and ask questions. They say the only stupid question is the one not asked.
I see your dilemma and would suggest this. Tell them to leave the top longer than the sides..(sides short, cut close). The reason for this is to add contrast, texture AND to elongate the roundness of your face. I think there is a reason why you were blessed with some curl to your hair. It gives you texture and will help with the fullness on the top to give 'height', taking away from the width of your face.
To combat the frizzies, there are so many products (even for guys to use easily, comfortably) out there available, one should never worry about remembering from shower to shower if they should bother shampooing this time or did you last time. You can have a "no thinking" routine where you shower/shampoo and apply a little product to top of your hair, then out the door.
To save you from buying a whole mess of products to experiment with (unless you want to do so), I'd ask that same stylist what he/she would recommend for your hair type. There are a number of hair waxes (squeeze tubes or sprays) on the market and even stores like Walmart has the Garnier Fructis products which I know are affordable that have "surf hair". You could apply this to the ends only of the longer hair on top, experimenting the amount, though I suggest only a timy bit, applying it to DAMP (only) hair. This helps the hair stand up if you like it that way or when it's dry you can finger comb it and tame it down a bit. Either way it muddies it up so that there is no frizz.
As for the coloring. Hmmm. I see the color of your goatee and your sideburns and it looks a lot darker than one shade. I take it this is the color you refer to for a beard? It looks reddish in the pic. Does it turn a red/dark blonde? Personally, I think it would be cool if while you are getting this haircut, long on top (about 2 1/2", 3" if very curly), talk to the stylist about some contrasting color on the top of your hair. You can go with streaks or all over color, just on the top longer hair. The shade to MATCH your facial hair. This would be an awesome affect.
Your hair grows faster on top, usually due to the longer length being combed and messed with more and if you decide you really do not like it, it will grow out quickly and you can get it snipped off soon enough. I would suggest you only do streaks of color on top though as it will shorten the height we are going for. Also maybe only go for a goatee. The dark on top of your head and on your chin are going to go against the elongation we are trying to achieve, though the coloring will improve.
Yes, do go to a stylist. Are there any bigger towns/cities close by? I live in and near small towns myself, yet I'm 15 minutes from a fair sized city where I can get things done more anonymously. If you had something like that closeby where no one knew you, you could go and get this done and then visit your small town barber/stylist. Once they see your new look, they will follow the pattern for you.
Good luck! Let me know how you make out! We always like to hear how people make out with their new styles!