Unless you're planning to venture out on the competition circuit, I'd consider an Amerique, or an FEC100, assuming your wife can be brought on board. The AQ will double your capacity and has some great features lacking in the 025. I owned one before moving up to the FEC100 (which I dearly love)
I began BBQ life with a $200 Brinkman offset. The drawbacks were maintaining an even temp, having to maintain a supply of wood (they chew thru a LOT) and as you say, you're chained to it. Overnight smokes? Plan on getting up every other hour.
You can find stick burners that are economical on wood use and maintain even temps. Jambo makes one that will fit your budget. Klose is another manufacturer that comes to mind. I would also consider gravity feed charcoal smokers such as Stumps or the Backwoods wood/charcoal burner. For the kind of money you'd spend on either of those, you're close to the cost of an FEC.
Whichever way you decide to go, talk to owners and do your homework.