For those who are curious, you can buy a chartlogging app for the iPhone. It's amazing, even shows bottom contours and was quite accurate. NiteFly brought his along when I took him out a few weeks ago.
That said, what will you do when it's pouring rain or taking waves? I don't think the iPhone is weather-proof. A hand-held Garmin GPS is cheap and weather-proof. I understand that you're on a budget- we all are, but cheaping out will get you injured, stranded, broke or all three.
The Easy Button- consider buying a towing service contract in case you get stranded. It's akin to AAA on the water and will save you THOUSANDS in towing costs if you run out of fuel, blow a sail, or bury your keel in the mud.
i2f- "mostly it leads to mishap"? Really? I don't at all doubt what you have seen but I am unsure that those unfortunates that you've seen comprise the bulk of people who choose to teach themselves how to sail.
Crazy- You're not crazy. Ask around in Illinois or down in the area of your boat for experienced sailors willing to come aboard to crew/teach you, and offer yourself up as crew also. Many folks will take you on for lessons for only a bottle of their favorite libation. I expect to be sailing with experienced racers this weekend myself. Read, read, and read some more. If you have Netflix and you're burned out on books, rent The Annapolis Book of Seamanship video series.
There are some folks here that like to tow around their little "cloud of doom" with them, but i2f is right. No matter what forecast you see on the laptop, no matter if you have the VHF weather feed on constantly, you are going to get smacked with a squall, a gust or a wave that isn't predicted. You've got to have your head on a swivel and constantly be prepared.
From one DIY'er, to another.
S/V Old Shoes
1973 Pearson 30 #255