I say go for it but my guess is that you may have to drop upwards of $2000 on a trailer. Even if you do spend that much or more I would say that you could have it paid for within a year. The reason I say $2000 is by the time you get a decent tandem with brakes, ramps, and possibly even a winch, things really start to add up. Do you have a gooseneck plate in your truck? If so it may be worth checking into a a small gooseneck flatbed. I would also watch Ebay. There is a company out of Missouri that builds what look to be very decent trailers and does heavy marketing of them on Ebay. Here is the website to their Ebay store:
Looky. Maybe for some further research it would be worth giving
Twin Cities Featherlite a call sometime also.