What an interesting situation. I assume you are trying to avoid subscribing to cable and that is a good thing cause it's like crack. The new HDTV you might purchase will probably have a digital tuner already so there would be no need for the converter box so you would have to figure out a way for the HDTV and the converter box (for the VCR) to share an antenna. Other than that I am thinking nothing really changes except you have a new TV. You would still need the antenna/converter for the VCR though and depending on the outputs available on the VCR you should be able to hook that up to the HDTV (75 Ohm coax, composite, component, S-video, etc). Might be some cable purchases in your future. Or ditch the VCR and go with an HD DVR. You may not be very happy with the quality of playback from VHS tape, especially once you get used to seeing your favorite shows in HD.
As far as the DVD recorder capable of timing programs, I am not sure what you mean. If you mean a DVR/PVR kind of thing like I suggested above then that would be the way to go. Check out this link to Tivo
and see if this is something you might like to try. I do not have Tivo but on the page I linked to it does mention that you can have the box as a standalone OTA DVR and you do not have to pay for their service. You will still have to use the antenna for this but you won't need it for the TV because you will be using the DVR as your tuner with pause, rewind, etc for live tv. I am not sure if you would be able to schedule any recordings as I think you would need an online program guide that would come with the subscription. Don't quote me on that though.
Hope this helps you out.