When you say the lift needs to go outside and work do you mean on gravel, disturbed dirt, grass, asphalt, etc If so an industrial pneumatic truck is NOT a solution for you. You need to look at a rough terrain forklift but the 10K capacity trailer won't do the job, you'll need a larger trailer. And for sure $5000 won't find you one that is worth shooting or would even sell to your brother-in-law. If funds are limited get it and a trailer on a "finance to own" contract or most often called $1.00 option lease (the lease part is a misnomer - you own it at the end of the finance term )