My wife and I have camped from Alaska to Florida using a small tent trailer which I pull behind my Harley . In North America, it is much better than hotels because you meet so many great people.
We have also ridden through Mexico and all of Central America, and would never pull a trailer behind the bike. We stay in small downtown Hotels in smaller centers. Very inexpensive, well located close to markets and all the local activities, and the bike is always secure inside the hotel lobby or guarded lot. Borrow a copy of the “Lonely Planet” from you local library to get an idea of what is available; the hotels, restaurants, costs, etc.
Also, you want every bit of acceleration you can get from your Harley when passing on blind curves, trusting the semi in front of you which is signaling you to do so.