ChiTwnPaul

I really enjoy making a guy cum, so far onyl orally, so for me I would hope the provider does. And as I have seen mentioned a few times, the mental aspect of a guy cumming in my ass is a big part of what I will be looking for.

Inherent risk is a part of this dance.  Mentally accept that first before you move forward with seeing anyone.
Never assume anything: Ask questions.  Not all escorts see tons of people on a daily basis.
A smart escort understands how to mitigate his STD risks.  You also need to do that same thing.
Bullet point:  Your sexual health is your personal responsibility and no one else's.
 
 

For the masseurs, it’s easy.  Just submit a pic of your back. 

Allow me to clarify: he should go to a Gay Bear Bar 🐻 or any Gay bar in a friendly city such as Chicago.
I forgot that there are bars in New York City or San Francisco or West Hollywood that are very clique, because I don't frequent those.  But as a middle aged obese man, I've always felt welcome at a Bear Bar or any Gay bar in Chicago with those fine Midwestern men and their values.  Nothing warms a man's heart like his first spit roast in the parking lot of a Gay Bear 🐻 Bar or in the basement of a Gay bar in Chicago.

Personally I don’t follow up with my clients because I want to respect their privacy. Some are seeing me on the down low and I’d never want to cause them a problem by following up after their session. If they send a message after with any kind of feedback then I’ll reply of course but I won’t do it unsolicited. 
I try to entice them back by giving a great service rather than spamming them. If they really want to come back then they’ll message me. 
 

Getting back to the original topic, and responding with a possible solution to @jtmick:
Start on Rentmen. Use the Search feature to filter by 'Preference: Bears'. Browse the list and pick providers. Then look if they also have a profile on Rentmasseur. Depending on your city, you should end up with a decent list of prospects.

With all due respect, the OP wasn't looking for advice on how to spend his money.  It's awesome you have been able to shed the excess weight, and that's a big achievement you should rightly be proud of, but the OP's immediate concern is about how he might be received at his current weight.

After being overweight for most of my adult life I don’t offend easily and have a thick skin. (Pun intended).  I’m not sure if you even read my post, but that’s just what I am doing, having gone from 477 to 250 lbs in three years.  My health is better than it has ever been the past ten years and my doctor tells me I’ve added years to my life.
The point of the post was to get feedback on what I should expect from providers at this size. 
I can assure you that any overweight person does not need to be told to get to a gym, we live in these bodies and whether or not we show it, we know deep down the effect excess weight has on our health.  Unsolicited advice like this is neither helpful or supportive.  

If you are in a position where you are worried about your weight then it should be a wake-up call to better spend your hard earned money in the gym and take it off. I speak from personal experience in this having shed close to 100 pounds over the past 10 years in multiple attempts. Sorry if I offend anyone but that’s my personal view on this. Health trumps pleasure.