First home brew - please help!

After your OG reading, I'd recommend not taking a hydrometer reading for at least two weeks. There's nothing to be gained from repeatedly poking your wort, unless you are collecting fermentation profile data. You won't disturb the fermentation, but you are introducing a (small) risk of infection. And you (usually) don't want to be introducing oxygen after fermentation has started.

 

Looks like you've got a pretty good plan going. No need to diverge much from the directions (unless they are somehow unclear, which was the case with my first batch, so I had to adapt the procedure a little).

I would highly recommend getting a wine thief for taking gravity samples. Sanitize it, dip it in the bucket or carboy, pull it out, then measure SG in the tube that your SG meter came in. I have been making brews almost identical to what you're making, and I haven't been bothering with checking the gravity till near the end of fermentation. I've left them all in there at least two weeks, BTW.

Yes, it's critical that you take an initial gravity reading when you reach final volume and before you put it away for fermentation. Again, sanitized wine thief makes this easy. I agree with vikeman, don't bother with taking another one for at least two weeks. You want to keep that lid on the bucket as much as possible, don't keep messing with your beer. It will ferment. It will finish.

The bottling wand is definitely a must. I fill the bottles till they just barely start to overflow, then pull out the wand. This leaves the right amount of airspace, and also gets rid of any residual foam from the starsan.

I have discovered that cooling in the sink is a pain in the butt. The first three batches I made I cooled in the sink with ice, and even with 20lbs of ice, it still took a long time (an hour or perhaps hours). Now I have a wort chiller and I can't imagine brewing without it.

I've been using bottled spring water and keeping one of the three 2-gallon containers in the fridge and using the other two for the mash and boil. The last one (the cold one) helps get the wort down to pitching temp when it goes into the bucket and you top to 5.5 gallons.

I have found that the most helpful thing for me is to make a checklist before I start and check things off as I go. This prevents me from missing any steps or forgetting something critical. I've been detailing my exact procedures and posting them online. Here is my latest batch, with detailed procedure. Your exact procedure will vary from mine, but the idea of making a checklist has worked well for me. You may need to make several drafts of the procedure before you're happy with it.

do tell how this comes out!

 

Hmmm, yeah I guess you're right, sorry for giving bad advice!