Savage rabbit, consolidate and update. I'm all about reducing the amount of vehicles that require inspection and insurance. I have a ton, (several dozen vintage bikes) but have no regrets about keeping them around as they aren't costing me anything or going down in value. It drives me crazy to see a bike unused and depreciating at the same time!
Having a shop do your work is great if you know them. They will do the work in a clean, well lit environment with the correct factory tools and manuals. It's best to recognize that you are not mechanically inclined and not screw stuff up or make a mess in a shop or garage you may not even have. I have a well lit shop with a wood stove and air lift table. I have only basic repair skills but enjoy light maintenance: changing chains and sprockets, fluids, certain seals, accessories, etc... I love working on the bikes. If you don't have the set up for it just take it into the shop.
I'm all in and rolling the dice with my new 990 R. One of the last of the breed. My 950 was great after working out all of the 2004 problems. It was a beast. We had water pump issues ( I think the shop said the impeller may have actually been in backwards or something, I forget but they finally sorted it out.) I like the idea of EFI and staying updated, thus the 990.
For ME: Harley's are one of those bikes that you don't really love to ride or own but miss them when you don't have them. I keep buying them and selling them. I've sworn off buying any more because I know I will just want to sell it then.
Now your Ducati, that's another story. I have a sweet spot for track bikes and recently got my racing license and competed in my first few CCS races. That's the best thing ever, besides dual sporting and road trips.