Newbie seeks feedback on research

You might consider a cd burner for your computer. Put the saved money into a better cd player, probably not a changer.
The real question will be if your chosen components match well with each other. That, you can only know by listening. If you can demo them before you buy, you will save time, money and stress. Be sure to listen to the music you like, not the audiophile discs that sound great. A system that impresses at first can become tiresome quickly after you get it home. Again, listen, listen ,listen.

I think the Kestrels are a great start in your price range.They were one of my first purchases and I loved them. I matched them with a Bryston B60. Excellent. They are fairly easy to match with a number of amps.

In regard to tape Vs CDR (stand alone Vs computer burner: I went with a stand alone CDR (burner) as it allows me to easily isolate it from vibration and to get better recordings. Another factor is that we seem to change computers every 2-3 years. I assume that you have a large cassette collection (as do we) and I am in the process of burning it to CD (well, I will start doing so within the next week or so). Many of the tapes that we own are "old" and will probably only make it through one decent playback as they have been in storage for many years. I was able to purchase a Pioneer PDR-W839 CDR, NIB and not a second, off of Ebay for $325.00 from a dealer that specializes in DJ gear. I was also pleased that after locating an IEC adapter (made by Harmonic Tech) and updating the CDR's power cord with one of the inexpensive Absolute power cords, that the playback quality has improved enough for us to use the CDR as a source (second duty) in a bedroom system (plus it is a 3 CD changer). Anyway, you would need a tape player to burn the cassettes to CD, but perhaps you already own a player or could borrow one if you decided to go this route. If your goal is to have "good" tapes for car use, then the added sound quality that you will get from a nice Nakamichi deck will be lost on most any standard automobile Hi-fi system. I have already gone through this 20 years ago and have owned two Nakamichi tape decks (the 550 and 600). If I wanted good sound I had to use the 550 deck in the car (it is a portable model). I also used the Advent 300 receiver as an amp/preamp and small Braun speakers (pre ADS) and sometimes Auratone studio mixing monitors. I figure that a quality (one that you are going to want to listen to as much as your CD source) cassette deck runs $600-$1200 on the used market, which makes the Pioneer CDR a good value. It can also be added at a later time and is not needed to get you started. Digital Audio CDR blanks (good ones) run approx. 75 cents each if you find them on sale.

Glen made a good comment above -- you also need to factor in some decent interconnects and speaker wire. Given your budget, I can't recommend a better line for both interconnects and speaker cable than Kimber. The 4VS and 4TC speaker wire is hard to beat at the price, and their PBJ interconnects are a fine buy (particularly if you can find them used). The other option for good interconnects is to buy the "Silver Solution" IC from HomeGrownAudio. If you are willing to do some soldering, you can get the kit, save some money, and have an excellent IC for the price.