Help! Where to start???
You mentioned that you intend to sail on lakes in the Midwest. Does this mean you intend to trailer? Do you need a swing keel? Trailerable boats can be different animals; especially if you intend to use a launch ramp and raise the mast with each outing.
I agree with Jeff that furling is probably not necessary on a boat this size, despite what many people might say. Without furling you need to accept the fact that you will have to scramble during sail raising/lowering when you are single-handed. You will also be subjected to decisions regarding which sail to use and when to change it. You may need to add some extra bits of hardware, etc. to accomplish all this single-handed, but it can be done. Anyway, you might find that most used boats in the range you are looking at are already equipped with furling and the expense to change back might not be worth it.
I prefer an outboard for the fact that you can pull it off easily and take it to a shop if necessary. I feel that an inboard adds to maintenance time/costs. Outboards, if reasonably small (15hp or less) can also be tilted up when sailing to keep a clean hull. However, in boats in the high 20 foot range you will probably find more inboards, especially in the used category.
When I purchased my first fixed keel boat about 10 yrs ago I went through many of the same questions you are asking. To keep it hassle-free I looked for a non-furling boat, tiller steered, driven by an outboard. Ended up with a Ranger 26. Not a bad boat.