Orlando, for having such a large population of gay people, has really, really shitty nightlife. Club Orlando seems to still be going strong.
I'd go back to Winter Park, as it's upscale, has an Austin-like vibe and is super gay friendly.
Tampa/St Pete/Clearwater has a scene, but it's super laid back. Also, the tourist contingent (also much like in Orlando) makes it tougher to find guys who stick around long enough to become friends (or regular fuck buds).
As a side note, I was a little surprised to see how many guys are available for rent or gratis (Grindr) in Tallahassee. It's the young male population of FSU and the apps there are always packed with some truly stunning gents. I'm there about once a month and have always had a ton of guys to pick from if the mood hits.
You are asking some good questions about how to get started. You're already using RM, which is your best bet for finding reputable guys to hire. While you can probably find some guys close to you by using the "Near me" function, you're a short ride on the LIRR to NYC which has the biggest variety of providers in a single city in the country. I'll try to answer some of the questions you posted:
How should I go about my initial contact? If the provider says he has a preferred contact method (i.e. RM Chat, Text, Call, etc), do that first! A lot of guys prefer text these days, because it's less intrusive than a call and more reliable than RM chat. If they don't give a preferred method, text messages are usually the safest bet. That said, while the RM chat feature is hit or miss depending on the provider, using it does enable you to post a review if you're a premium RM member.
Is there a good protocol to follow to get a guys interest and show him I am a good, respectful, kind and serious client? Good question! The best way to show him you're a good, respectful, kind, and serious client is to send messages that are respectful, kind, and serious. A solid first message would be something like "Hi <name>, I saw your ad on RM. I'm planning to come into the city this weekend and would love to meet you. Are you available Saturday around 7?" Be patient and know that some guys are going to be more responsive than others for any number of reasons. If a guy doesn't get back to you in a reasonable timeframe, move on to antother or try again another time.
Are there ways I can filter out some guys so I only connect with guys who are a bit more professional, serious and customer service focused? Some of biggest indicators would be a well written profile that has been active for some time, with good reviews (using a proxy to see RM from a non US based IP will let you read review text which can be very enlightening). Posting questions here about guys who catch your interest is also good way to weed out flakes (though not a guarantee).
Am I just spoiled by women sex workers and have to adjust to the reality there are fewer options this way? Maybe. Sex work in the heterosexual world is orders of magnitude larger. Still, there's plenty of great guys in the business, just take your time and do what you can to check a guy out before trying to set up a meeting.
