Hey Brett
Funnily enough, I have pretty much followed the exact same path as you. I was/am very interested in astrophotography and have learned quickly that you can outgrow things very quickly and realise you've got the wrong equipment for the job.
I had a fujifilm point and shoot camera as well, and started taking shots using the afocal method which was very rewarding... when I got one out of 20 shots steady enough! It was great for the moon, but that was about it. Then I got a Celestron Neximage - a good planetary imager as it uses video, but it's not going to help much with DSO stuff.
I was thinking about a CCD camera as the next step, but for the price and my level of experience, I couldn't justify it. So I went for the DSLR option as it serves the purpose of a very nice "day" time camera as well. So I also opted for the 500D, but my parents were in the states recently so I asked them to pick me up the US version which is just badged as the EOS Rebel T1i. Just on that note, I noticed you said "I didn't need the HD recording side of it (like the 550D) as I have a HD camcorder for that." - You do know that the 500D does HD video recording as well right? Just turn the mode knob to the film icon!
Anyway, I had been using my friends 450D before hand, so I got the required accessories for it (this is for prime focus) - You'll need a T-ring adapter. This goes were the normal camera lens, and from that you'll need a "camera" or "t adapter" - I found a lot of websites call T-rings "t adapters" and also call camera adapters the same thing, but basically its the small tube that screws into the t-ring, and then goes into your focuser.
NOW - I have (about to put up for sale) a 5 inch Black Diamond SW Mak - for the afocal method this works really well for planetary imaging and was easy to reach focus. I only tried once, but I managed to get some blurry long exposures of a few star clusters, but the guiding is a whole other issue. I also have an 8 inch SW newt - I was super excited to try out the DSLR on that, and then ran into a problem straight away - I couldn't reach focus! I then, unfortunately, found out that newts can't get enough inward focus, and I read about some mods that I really didn't want to try - one being cutting the tube to move the primary mirror up, or to buy a new low-profile focuser which was going to be costly. Thankfully, Vince from myastro shop told me to hold off on spending my money and just try adjusting the primary mirror to move it up from the base of the scope using the thumb screws, and then just re-collimate it again - it worked! The reason why I've written an essay on this is because, based on your footer, it looks like you've got a dob so you may run into the same issue.
Being a dob, you won't be able to take long exposures as tracking is going to be an issue, but you can probably get away with 30 second shots and stack them later.
I've probably missed a lot because I've learned 10 times more in the last few months! But hopefully that helps you out a bit more. From what I've heard, positive projection (having an eyepiece between the SLR and the scope) is a bit of a nightmare, so I'm staying far away from that for now. I'm selling my mak as I got an ED80 to replace it - a better scope for imaging IMO, but of course a sacrifice for apature.
Hope that helps?
EDIT:
Just a couple more things:
- Get a remote if you're going to use the Bulb setting (for exposures longer than 30 seconds) otherwise the the camera will pick up the vibration when you press the shutter button. These remotes are super cheap on ebay - and the 500d has infrared so you can get a wireless one! However, as you'll probably be doing 30 second subs or less, you can use this as the exposure time instead of Bulb, and use the camera's timer feature so you can press the shutter button, and then it will wait before it starts taking the shot and thus eliminates the vibration issue.
- If you want, grab a spare battery if you're going to be out for hours at a time. You can get an external power supply so it's not running off batteries, but then you're going to need something to power the power supply
- The adapters I mentioned above can be purchased from any online telescope shop, I got mine from Bintel but any site will sell them for around the same price. Just make sure you get a T-ring for the EOS body cameras
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