Well if you don't have any business in San Diego or SoCal you may as well stay.  Ticuan Hotel opens again on the 20th and Hyatt Place is nice as well.  Both are escort friendly.  Pay after your date with any escort service and the price posted is all that is expected.    

I am sure others will have more to add, and I will let the others finish.

1.  I suggest staying in TJ,  It's safe and crossing the border daily will be tiresome and eat up a lot of time.

2.  Tijuana has lots of good hotels as well as flea bags, more of both than there's time to name.  The Ticuan Hotel (which closed for a fire) may re-open before you arrive and would be my first choice as it is probably the best combination of location and luxury.   It the Ticuan is not open then I suggest either the Villa Zaragoza or the Pueblo Amiigo.  The Pueblo Amigo is the nicer, but the Villa Zaraoza (like the Ticuan) is downtown, which is more convenient.  

3.  CUMINTJ (together with Mexico Lindo Bar and Hot Tijuana) is a top tier escort agency.  The top tier agencies provide GFE services and don't play games--such has employing chicas who ask for more when they arrive.

4.  Tijuana has lots of good restaurants.  In downtown Tijuana Centenario (on 8th between Revolucion and Madero) has good, inexpensive Mexican food.  The restaurant in the Caesar Hotel (on Revolucion around 5th) is a good, downtown upscale restaurant.  The Zona Rio financial district has a lot of good restaurants such as Villa Savarios (perhaps the best overall restaurant in TJ), Pampas, La Diferencia, and Chan's Chinese.  The Grand Bisto in the Tijuana Grand Hotel is perhaps the most elegant in Tijuana.  Rabelos Los Arcoso, and Durazno Nego (three good seafood places) as well as Cien Anos and Casa Placenica won't disappoint.