SirKenLDesign

I'm not usually an escorted kinda guy.  I might not even know what to do with one, in all honesty, but this guy is checking quite a few boxes for me.
Toyboyss - Male Escort, Gay massage - Ocala | Rent.Men
RENT.MEN Toyboyss Gay Escort in Ocala, Florida, available for Gay Escorting,Modeling,Erotic Massage. |... Does anyone have any experience or feedback? DM me if you must.  I'm very curious,  and going to need to make a decision very soon. 
 

There have been "pimps" who work with make tourists for years. They can provide a good service but at a price. there is a bar called Marlowe's that is excellent . I have never even heard credible reports of violence against gay tourists. The Colonial zone is well accustomed to it. As are the surrounding areas -all Dominican hotels check the ID of anyone who goes into the hotel with you. In fact, they keep the cedula at the desk until the guest leaves. Often, they will call up to verify. 
the Colonial zone is indeed. a world heritage site. It is the oldest continuously inhabited European city in the new world - the first cathedral in the new world. The place was, literally, founded by Columbus. 
You are only warned, as do here, against Grindr. It can be very good but if you take yourself outside the system at least have the sense to meet at Paco's ( coffee shop) or Marlowe's. 

I went to Santo Domingo for a few days one fairly recent winter and we stayed in the colonial zone. A very nice hotel close to the river (canal?) and some traffic of what I assumed to be local trade of both genders, that is, older gents bringing up the elevator young males or local women presumably not related. There appeared to be a group of American men, not sure if they were like a buddy pack, that engaged with what appeared to be a local “sexertainment” middle man at times accompanied by a few young females. Out in the open yet discreetly, and the staff knew the deal. But it didn’t seem smarmy and I thought it was a system that worked out for everybody.
However, one older male hotel guest ended up on the lift with me and I thought the local youngster with him was quite young, though I assume legal age because I am told that non registered guests ID are checked. Perhaps it was not a sexual transaction anyway.
The area of several square blocks seemed almost UNESCO world heritage badged, maybe it is? I thought the overall feel as far as the area not including oceanfront was somewhat like Puerto Vallarta, so not like a cloistered hotel property but comfortable and an appealing environment and certainly a lot of interesting sights and places to relax, particularly if you do not need or like lollygagging on beach sand or slowroasting your skin by a pool. As long as the weather was nice it was very pleasant and no boredom set in. There seemed ample potential for picking a favourite public terrace to perch and chill out, safely, with a vibrant mingling of local families and visitors.
If there is a process, overt or subtle, for engaging trade within that context, it certainly appeared to be a user-friendly district with good amenities within which it could be done comfortably, not risking life or limb.
Overall, a top 3 experience of winter getaways over a few decades. I’d do it again. 

Sad to report that Perverts is closed. Signs on the building tease a new club "BMine" that looks to be a higher quality male strip club. Sad to see this low key spot get gentrified but change is the only constant. 

Southern California Men's Bondage Club
WWW.SOCABONDAGE.COM  

Bumping. I would love to find a spa type environment with extras

I visited the Parliament House last time I was in Orlando.  What delicious fun.  Too bad it’s gone 

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.