Any suggestions for a fairly easy to use backup program with these specifications--free or pay?
With your specs I don't think there are any I could recommend. If you're concerned about Windows Vista settings & such you want/need a full disk/partition image backup, but that type of backup is neither file-based nor stored in an open format. -- 2 of your requirements. OTOH restoring a file-based backup on a new drive won't give you a bootable copy of Vista just as you had it. IMO you are better off using 2 strategies, one for Windows & installed software, another for your genealogy data -- treating the 2 separately you then have many choices for the genealogy stuff, including cloud storage.
There are basically 3 kinds of backup apps/methods: 1) Make duplicates by writing to more than one hard drive at the same time -- this is what many big companies do, because if something happens to a drive or even a data center they can switch to the 2ndary setup & be up & running more quickly. With the advent of the cloud, & the resulting battle between companies like Amazon, Microsoft, & Google to be your cloud storage provider, storing &/or mirroring data on the cloud is getting a lot of hype/emphasis. I think most PCs allow you to create a RAID setup to do mirroring, or more expensive external multiple drive housings can use the same sort of RAID setup. I believe something similar will be included in win8, but not sure it will appear in all versions or SKUs.
2) Make hard drive or hard drive partition image backups. Because you're dealing with raw data [the 1s & 0s] backup & restore happen as fast as possible, & as you're not including any of the free space on a drive/partition they may take up roughly 1/2 to 2/3 the space as the original files. The downside is you lose the speed advantages of dealing with raw data when/if you you want to work with individual files/folders.
3) The most primitive, least efficient backup method copies files/folders, usually with some sort of Zip file compression so the archives take up less space. Nowadays it's mainly useful for quickly/easily backing up just one or a few files/folders -- there are several apps that back up your docs, e-mails etc. this way manually or on a schedule, & because you're backing up much less data, backups/restores take less time than working with an entire drive/partition worth of data [even though on a time per file basis they are the least efficient]. This sort of backup app is common enough that it's even included or bundled with Nero, Roxio etc. Some advertise that they'll do a hot backup, backup even Windows files that are in use, but since restoring one of these backups to an empty/formatted drive/partition won't give you bootable Windows, I've never been sure why that mattered.
... a backup program that will do a little more and will possibly help me to find program settings that I should be backing up...
I'd strongly suggest a disk image backup since that's the only solution that'll let you put your desktop system back the way it was exactly if you get hit with a virus or hard drive failure or Windows just breaks after for example a software update. The image or archive will be in a proprietary format since there isn't an open standard like Zip or 7zip that could be used, but as this backup could be written to DVD or Blu-Ray discs, including the restoration program, that shouldn't be a big problem. Personally I prefer Paragon & Acronis apps. Acronis is faster from a boot disc, & available free from many hard drive manufacturers if you have one of their drives, even in my experience if it's external, as the app just has to find 1 of their drives & it'll run -- you can also sometimes find Acronis software free after MIR. Paragon usually has a limited version of their backup apps free on GOTD, often when they release a new version. Paragon also has somewhat frequent giveaways through magazine &/or blog sites, & has fairly regular sales. Some people like the free disk/partition image backup software from EASEUS [I don't, compared to Acronis & Paragon] & the EASEUS app is always free. Windows 7 [& presumably win8] has a decent disk image backup built in.
I do a lot of genealogy research (I'm retired) and don't want to lose any of that data--hence the 2 USB drives (one 250GB and one 500GB).
Fact is most of the files/folders on a PC/laptop don't change -- only change when you add new data files/folders or update/add software. If you've got GBs of files, IMO the most efficient way to protect your genealogy data would be to put it on a separate partition or drive & then back that up very often &/or mirror it to another drive. Being on a separate drive/partition also makes it much easier to manage, maintain when upgrading Windows, restore from backup etc. If you have broadband & a relatively small amount of data OTOH you may want to skip most this stuff & just use free or paid cloud storage. Because you're backing up data rather than system files, you can back up individual files/folders or go the partition image route. To access individual files/folders in a Paragon backup archive I routinely just mount the backup archive as an added disk/partition in Windows, then copy/paste, but it can still take longer than extracting the same files/folders from a Zip or 7zip archive, & I don't believe all versions of Paragon backup apps can mount archives that way. Restoring an entire image of your data partition would be fast/easy, but any changes since that backup was made will be lost unless you copy them somewhere else beforehand. And finally another factor to consider is the speed of your external drives & their connection to your desktop PC. USB 2 is Slow & more trouble prone compared to USB 3.0 or eSATA. I don't know what you have, nor how important transfer speed is to you, but you may find backing up a partition image faster than a file/folder based backup, or not -- depends on things like your AV software, your PC's USB chip, your external drive electronics, & the backup app. Try it both ways [partition image & file based] & time it, also checking the results to make sure what's written to your external drive is error free.
Note that if your drives are USB 2, one potential option is to swap external drive housings if you have problems or want more speed, but you'd have to research to see if it was possible &/or easy to remove your external drives from their cases -- SATA/eSATA or USB 3.0 internal/external docks & external housings start in the $15 - $30 US range. Note too that backup apps often install drivers, & those drivers are not compatible with all software, so research 1st, checking known incompatibilities before installation.
... I prefer to overwrite newly changed files...
Not 100% sure what you mean but Hopefully this will help... Whether you're doing a file-based or image backup there's something called an incremental backup, & what it means is that the backup software will 1st compare files & file versions between the source & an existing backup archive, then 2nd, it will only backup or record any changes. Storing archives takes up more space since you're storing older & newer versions of the same file. Because of the file comparison it also takes longer to process everything. OTOH if it takes a really long time to transfer & write the backup to your external drive, transferring/writing less data, i.e. performing an incremental backup may be worth it. A regular backup won't check what you've already backed up, but puts everything into a new, separate archive. With regular or incremental backups it's usually up to you to delete old backups to make room as needed -- since incremental backups use, rely on a full backup as their base, you'll more often delete everything & start over with another full backup, then perform incremental backups based on that. When it comes to restoring a backup, you usually have a choice to overwrite existing files, or restore the backup to a different folder or partition & then move the restored files you want where you want them.
If you're saying that you want to store a backup that's always identical to what you have on your hard drive, i.e. versions of files always current, you want a disk mirroring setup -- there are syncing apps that watch a folder(s) & copy any changes somewhere else, or get an external RAID housing with 2 or more drives, or check out Windows Home Server or win8 for mirrored storage features, or read up on adding/enabling hardware RAID on your PC or setting up a software version in Windows. The external RAID setup might be easiest, but it's also most expensive. If you've got broadband & your genealogy data files don't take a lot of space syncing them with cloud storage may be a great way to go -- you'd still want local backups since even with redundant hard drives cloud storage has failed [though rarely], but could be reasonably assured of having a mirrored backup available 24/7. Which brings me to WR's mention of backup &/or syncing apps running in the background...
Basically these are backup or syncing apps run on a schedule you set, backing up/syncing files/folders/disks/partitions you set, but doing that job on a slow, very controlled pace so hopefully they won't disturb you. Pros = you don't have to bother running a backup, or remember to run a backup, plus Paragon's System Backup for example can add restoring that backup to a boot menu in case Windows won't start. Cons = doing something like typing this post the resource drain wouldn't be noticed, but if I do something resource intensive, it very well might be. And running slower it takes longer to complete, so if you're backing up a Lot of data, you're unprotected for a longer period of time than if you bit the bullet & did a full speed backup right off the bat.