"Main question is will taking out two large separate loans be hard to do that close together?"
Since none on here know your financial history and current financial situation, that's a question that no one here can answer. Not unless you wish to post your bank account figures, earnings for the past three years, number of dependents, number and amount of all loans, etc.
However, if I were looking to buy an trailer/5th wheel and a truck to pull it with, I would definitely buy the trailer/5th wheel first. Too easy to buy the truck first, then buy a unit that's too big to be easily pulled by said truck. Buy the tote first, then buy the toter. That's my thought.