if the model number of the unit contains 1xx and it was made in teh last 6-7 years, it is a el cheapo model. Dealer models will be LT/LX/X3xx for lawn tractors and GT/GX/X4/X5/X7 for garden tractor models.
i have no clue about the simplicity, so i will leave that for others to answer.
but as far as the Deere units to get into a "real" deere, meaning one sold originally ONLY at a dealership, you will either have to get real old for that price range or raise your price. check machinefinder.com for machines in your area, you may run across a deal there.
as far as the Husq/Crafts/AYP/MTD machines, pretty much any of them in that range are equal machines. i do not feel comfortable recommending any 1 model though, nothing against them i just don't have enough hands on with them to say one is better than another.
teh flat land and leaf vac could be handled by pretty much anything. the 2 acres means that you will rack up time on teh machine and low end machines may wear out sooner than desired. or you could find one that last 30 years, that is the gamble you take!
most of the Deeres I've seen in this price range have been just numbered models like 214, 314,etc.