Welcome to CRT, SK!
Every reply to your questions so far seems to be right on the money.
I have stayed at Amistad, Castillo and of course, the SPortsmen's Lodge. Each hotel has its own advantages.
Rooms at the HDR are shabby. No, worse than shabby. Many do not even have windows, being in the interior of the hotel. The rooms are small and because of constant use, very beat up. Yes, there are hookers in the bar/casino 24/7, and if you get an urge at 3:30 in the morning, it's a quick elevator ride down to the action. However, drinks are overpriced, IMHO.
The Sportsmen's, while I love it is starting to show signs of wear and tear, even in the "Modern" section, but is much nicer than the Hotel del Rey. It's smaller, and is located in a residential neighborhood about 1 km. from the Hotel del Rey/Key Largo club. While the SL lacks the 24/7 aspect, the bar is frequented by lovely ladies from mid-morning until midnight. The food in the bar/restaurant is good and farily priced. The bar features TV's for watching sports, a pool table and a Golden Tee golf machine for fun. Service is friendly and top-notch.
Hotel la Amistad has undergone extensive renovation over the past three years and is now perhaps the most luxurious of the hotels mentioned (with the exception of the SL's new Mansion wing, which is expensive but spectacular). No working girls on-site, and they do have a "1 chica per visit per guest" limit in order to maintain security. Again, excellent staff, and the breakfast included with your room price is the best of all hotels mentioned.
The Castillo feels like you're staying in someone's very nice home. Furnished with antiques, a broad curving staircase and several unique rooms, the Castillo is probably the best value in terms of price. Pay cash, show your CRT-VIP card...and it's the least expensive of the options mentioned.
No Spanish? Dude, no problem! Visit the Sportsmen's around Happy Hour, connect with some wing men, and let the good times roll. Many of us speak Spanish, and most of us are more than happy to help a new guy.
Asian? I have a different take than some. Recently, Chinese business interests have been putting a lot of cash into the C.R. economy. You may not be Chinese, but frankly, the round-eyed chicas can't tell the difference between a chino, japoneso or koreano... and will think you're a high-roller from Beijing.

You may actually get more attention than some Caucasians.
Friend, do yourself a favor. Pay the $39.00 for V.I.P. membership. Savings at the Sportsmen's (20% for the room rate for the rest of Green Season/10% on all your food and beverages), Amistad (special deep discounts for CRT V.I.P.s) and Castillo alone will pay for your membership in just a few nights' stay. Plus, you'll get free strip club admissions, discounts on tours, discounted MP sessions, a printable map of all the best places, access tothe photo galleries, and access to a more exclusive section unavailable to the general public.
Welcome! If I can answer any questions directly, please send me a private message (PM). I am more than happy to help if I can.
