you BOTH have to look inward.
What do you get out of your encounters via the hobby.
Meaning, do you have a great civilian life and the hobby is about the sex of it all?
Do you prefer 30 minutes over 2-3 hours?
Does your home life present issues for you logistically or emotionally?
Are either of you introverts that prefer most of their time during any given day to be alone doing what they want without others in their hair!
Both of you have to be very comfortable with the plans you make, it is very hard to hide a major difference in life styles for an entire weekend.
I have done a vast number of longer dates from 24 hours to 2 weeks and only had 1 somewhat challenging situation arrive and it took all over about 30 minutes of compromise to work it out. That is VERY important as well, can you make change on the fly without being upset or rigid in your ways. LIFE happens and can ruin an otherwise good plan.
One thing you have to be absolutely clear on..how safe do you feel with each other? If you have the same room and will have your purse wallet unattended during your stay,, do you TRUST the other person with that situation, how will you handle it?
In any case BE HAPPY with a plan you both put in play, IF either of you are not 100% happy with the suggested plan DO NOT DO IT!
Example is what has been mentioned by others in this thread.
If one of you wants separate rooms and one wants to stay in same room, walk away!
Plan well, think it through, then have fun!