Don't worry too much about your looks. There aren't too many of us who are 10's (or 9's, 8's or7's!).
Knowing some Spanish will put you far above the crowd of occasional visitors. Be sure to study the "special" phrases in the Newbies section that you will need to know for negotiations. They don't teach those in class!
If you are planning to hit the gulch after you business is completed, why don't you just consider staying there? It would simplify matters considerably. You wouldn't have to taxi back and forth to the suburbs and you would have a place to take your chica(s). There are many reasonably priced hotels in the area.
If you plan to make short visits to the gulch, visiting some of the MP's might be a good option for you. You wouldn't have to rent a room. HLH has a bar and a good selection of girls. Many of the other MP's don't have much in the way of facilities for their guests.
If you do decide to hit the HDR or venture around the gulch, I would recommend that you try to find someone to be your wingman. Many CRT members can be found at various hotels around the gulch but especially in the HDR and SL.
Be advised that you may encounter a decrease in the number of girls that are working at the end of December. Many of the girls go home for Christmas and do not return until Jan or until their money runs out. The freelance action in the HDR can sometimes be frustrating if the girl/boy ratio is not good. Often the girls will be tough to budge off of demanding cien.
Hope you enjoy yourself!