If this was my approach, most likely my time wouldn't be spent woodworking right now. My income at the time didn't allow the purchase high end tools.
One of my posts in the Sticky: Neanderthal wisdom/FAQs addresses what to look for when buying on ebay. It can not cover everything some charlatan might try to pull, but that is why one needs to ask questions and pay attention to feedback and what the dealer is selling.
This will help with a lot of "what to look for when buying planes."
http://www.sawmillcreek.org/showthre...gs-to-Look-For
Here is one on getting started with hand planes:
http://www.sawmillcreek.org/showthre...th-Hand-Planes
As said earlier, if my process started by purchasing high end planes, even a block plane, my woodworking enjoyment would have been thwarted. Yes, the OP did say they had $800-1000 to spend. That is not a reason to spend that much. Spend some of the savings on a guilty pleasure for the significant other and it will be easier to spend more on tools in the future.
My method may be backward, but my high end plane purchases have been limited to tools not available at a decent price on the secondary market and only after learning how to work with the old second hand planes.
Sure there were some struggles and disappointments, but the lessons learned by going along this path have been invaluable.
If Jared has a good income and can support all new tools in his shop, then it may be the best path for him. If he is like me and spent a lot of time eating weenies and beans to save up his money, he may want to consider second hand tools.
He did state:
An old Stanley #4 and #5 from a reliable dealer would be a good choice. Otherwise both from either LV or LN would be great choices.So what tools should I buy to get started with my $800-1000. I only want excellent quality tools, even if that means just buying a few at first and adding some more every couple paychecks.
jtk