Sure.
Needless to say you must anticipate a conflict at every stage of your long time. Always be able to travel or resume your travel without anyone's help and never pay many days in advance. This is why a ladyboy from a bar is problematic since her bar will require her to pay for the BF upfront. The best deal is to book her for 3 days then ask her for additional days. You will have to add the BF when paying her. (I did it once).
Example of a conflict that happened to me. That was my first trip and my first ladyboy in Thailand. I had a very interesting daily rate but my love mate would make me spend a lot of money to get drunk every night.
I first asked her to go to Issan, but once in her town, she knew the best bar in town and kept on drinking. Just for one word one evening (nothing to do with alcohol though), she became mad, took her money from her bagage and went to an hotel bar and got worse than drunk drinking whiskey all evening long. When she knocked the door of my hotel room, I hesitated to open. I had tried every soft argument to bring her back to a positive attitude. I actually felt very stressed. She had brought me to the middle of nowhere and I didn't know how to get out of it.
I refused any compromise on one point though : she had to stop drinking or I would go without her and I asked the hotel to check out on the next morning. I didn't know how to travel, but I was ready to do it alone.
I traveled alone in many places of Thailand since then. I realized that this ladyboy taught so much about deep Thailand but this experience also taught me not to be shy to travel alone.
One more tip : write down in a pocket note book every amount of money you pay her for your agreement. Write down the day, the time and the amount of money. Be honest and you will be stronger if she complains you haven't paid her (happened to me once too).
IMHO, you should always go for a ST before even talking of going LT and never bargain a LT with some one you don't know.
I had decided I would do it on my own if she didn't accept my conditions : stop drinking and don't argue on my choice to go to another city. We had a great end of LT.