I'll probably say "yes", as a blanket answer... but you have to be aware of potential diminishing returns as each session goes by, and by then choices have to be made whether to continue the relationship/arrangement or not. As long as you're both level-headed, respectful and professional, repeat experiences can provide better services as more trust is gained. But people pointed out, there is the risk of "catching feelings", and that's a hazard or a blessing for both client and provider. But it's more than that, where more of your personal lives start to intermingle more.
For whatever reason one dabbles in this trade, both parties are from different worlds. And the trade itself sells "fantasy", not "reality"..... that's why you have to be level-headed.
The more you see a provider, the more familiar you get, the more trust you get, the more benefits you get, the better sex you get..... then the friendship ensues out of nowhere.... and the more favours are requested, more errands, more gifts and loans, more 'helping her move a couch', more 'can you pick up some eggs before the session so I can make breakfast after", more "I bought a toothbrush just for you", more "how come you never take me to the botanical garden?", more "will you leave your wife for me?", more "I need $1,000 by the end of the day or my gangster ex-boyfriend is going to get me", more "I'm ready to settle".....and then at any point, you have to step back and say, "Whoa, I just wanted some strange, and you were really good at giving it. But since when did we get THIS close?", and then you stone-cold ghost her (which I did speaking from my own experiences),... or continue the relationship, and allow her burdens to become yours if your willing; maybe you sought providers to change your life, while she was looking for a way to change her life too, and things just started to click, right? It can happen that way too.
So yeah, the sex can be great,... but is it great enough to merge your worlds down the line? Eventually there is only going to be so many of these regular sessions before that choice is imposed on you one way or another.