Hi Again!
All righty, well after I learned so much from you all I brought it home and changed around my parent's finances (with their opinion/permission of course!).
In the beginning, they had--
Delta AMEX Platinum (not using any of the perks, including companion pass) ($17k CL)
Capital One Business Spark (needed for non-AMEX businesses, no annual fee=Dad was happy)
Costco AMEX ($13k CL)
Bloomingdale's Reserve ($10k)
Due to the fact that they were not using any of the Delta AMEX Platinum perks, I applied my Dad for a Delta Gold, because they want to have the baggage perks while they use the rest of their SkyMiles (about 200k left). I got them a great sign-up bonus and no one-year annual fee, which even though they have the Delta Platinum, AMEX has promised twice, they are considered separate cards, so my parents will receive the sign-up bonuses. This will allow them to put those Skymiles to use for one year with no annual payment, yet still the baggage perks. I expect them to close the account when the AF becomes due, unless of course AMEX is willing to compensate them via points/credit.
I then got them into Chase. My Dad banks with Chase (joint account) and I know the UR 1x1 transfer would be best for them because they usually fly SW and Delta (because of Skymiles). I decided to switch them to UA instead of Delta because (after extensive research) the point value on international flights is much better via UA than Delta. With this, I applied my mom for a CSP, Freedom, and UA card. I am to hear comments/criticism from any others who use this combination, but these seems like it is a great combination to have for international travel via UA. (They even have some great domestic award tickets...)
It is going to take my parents some time to get used to using what they have to when, etc. but they are onboard with what they have to do (for the sign-up bonuses), as well as paying most of their non-credit card accepting bills through BlueBird.
In the end, my parents ended up with:
Costco Amex ($13k CL)
Gold Delta AMEX ($13.5 CL)
CSP ($30k)
Freedom ($28k)
UA ($10k)
Capital One Business Spark (only having them keep this because there is no AF so no reason to close it--sock-drawered)
Bloomingdale's Reserve (no AF=sock-drawered)
In time, I will have my dad sign up for all the same Chase cards to get the same bonuses, but I believe they are set now with 145k points! They will also sign up for the Hyatt Chase for 4 nights free, which will help with their Europe trip via Skymiles.
Please let me know if you have any other ideas or helpful tips! 
You all are so helpful, I couldn't resist asking just to make sure!
Does your dad have a business where he can apply for an ink bold? Its got a nice bonus and benefits (grat for paying phones/internet/cable with). Also I think you get two UA lounge passes per year with it. Also, in the same vein maybe a Chase Ink Plus (a revolver) for additional bonus miles. There is no way to downgrade the Ink Bold to no annual fee, but what can be done is keeping the ink bold and getting rid of the CSP when the annual fee becomes due if Chase won't waive the fee. This way you would still have the ability to transfer UR points.
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