Hello Shawn,
Tried to read down through what requirements you have and will tackle them in order. For getting started 45acp is one of the easiest rounds to start on, you are going to save the most money over factory with the 44's and 45 and rifle rounds.
The Forster Co-ax is a great press, the only downside I ever saw about it (besides the priming system and price), was the long handle stroke for small handgun calibers. For an alternative I would suggest the RCBS Summit Press for about half the price of the Co-ax, and then get a RCBS Automatic Bench primer, much easier on the hands fast, and gives you a great feel for seating the primer. You can add the Hornady Lock-n-load kit for faster die swaps if you desire. Only downside difference I see is that you would still need shell-holders.
I see the Redding T7 has been recommended, while it is a heavy press, it does not weigh 86lbs. Think it comes in around 30lbs--so it is still a heavy chunk of iron. The press is really well made, strong smooth stroke. You can even add a case-activated powder measure (strongly suggest RCBS Uniflow with the Hornady Case Activation kit). The only downsides that I noted, while you can add 3 pistol calibers to the tool head--I found I could not fully turn the turret all the way around as the case-activation kit would not clear the rear support of the turret. The turrets do not take the Hornady Lock-n-load quick change bushings, and the turret heads are very expensive--which you would need a couple to cover all your calibers or just change the dies.
I've heard a lot of good feedback on the Forster Case Trimmer. My experience has only been buying and selling used ones. My trimmer is a L.E. Wilson and I really like the trimmer, accurate, repeatable results, and nice square cuts.
Any chamfer/deburring tool will work. Have a Redding that works well, but can't say it is any better than the Wilson made RCBS one I have.
For a powder scale I had a Redding #2, and found the base to be very tipsy, plus the adjust leveling screw was under the beam. Loved my RCBS 5-0-5, and would highly recommend. If you are looking to save some money you can check eBay for Ohaus scales, as they make them for RCBS and they typically go for a little less money. I currently use a RCBS 10-10, and it is top-notch.
For powder measures, I would highly suggest the RCBS Uniflow as I found it extremely accurate for handgun rounds. If you are considering one, make sure you get the combo kit with both the large and small metering drums (rifle & pistol.)
For a trickler, I like my Redding--as it is a nice heavy stable unit--but any will do the trick.
Don't have any experience with ultrasonic cleaners, guess they work. I have had good luck with a Lyman Pro1200, and put tons of brass through it with cheap media.
I would postpone getting a Chronograph. Suspect you will be using starting loads and proceeding with caution. If the speed at which you are putting lead down range really concerns you--you can always get one later.
Redding dies are nice, but for handgun I don't think you are going to gain anything over any of the other manufacturers. I've always had good luck with RCBS, and I know a lot swear by Lee (or at the lock rings

) For rifle dies, a lot of people like the added alignment sleeve of Redding, Forster, Hornady. Again, I don't think you can really go wrong here.
Imperial Sizing wax-without hesitation YES. Works great for rifle, and they are not lying when they say a little goes a long ways.
A lot of people love the universal depriming die, probably a good choice if you are going to deprime before cleaning. The die sets include a deprimer, and I deprime after I clean my brass--so I didn't see the need to buy another die.
Missouri Bullet Co. is a great vendor, and I am sure you will be happy with their products.
Lyman and Hornady both offer nice reloading manuals. Won't hurt to own both and more.
When you starting getting your equipment, sometime it helps to use C-clamps and mock up where you think you would like everything before you starting drilling and mounting.