In my opinion ....
Everyone collects at different grade levels. From your post I have read, you do a lot of jumping around.
There really is not need to be in such a hurry. Decided what you want to collect and in what grade and then
come up with a plan/program as to how you want to put that set together.
For me, I started out like you and many others .. something like, start a set and fill as many holes as possible.
If you want some advice. For example for the
Kennedy half dollars.
Decide what grade want. Do you want them slabbed, albums, capsules or 2X2's.
For me, if I am doing modern coins, I think you should go for high grade MS 65 or better.
A good way to start would be to get a Dansco P and D only album. The highest priced coins
in this set would be the 1964, 1964 D, 1970 D. These 3 can be had for less than $20 in BU grades.
I did most the rest of mine from mint sets. Of course doing them from mint sets you will run into
the issue of business strike and satin finish. I just put them in together and have no problem as
to how it looks.
Then if you decide you want them all .. you will have the proofs and silver proofs.
These will cost much more then the BU coins. And to me I would store them different.
Go with capsules like airtites.
The crown jewel of the Kennedy set is the 1998 matte proof that comes with the RKF commemorative dollar.
This coin right now seems to be in the $200 range.
Why do I like high grade modern coins over circulated coins. They fall in line to what you have been saying.
You like the
Kennedy half dollars but you want them to increase in value also. Common coins in higher grade,
go up in value more than common coins in low grade. An example of this would be Lincoln wheat cents. Most common Lincoln wheat cents are bought and sold from 2 to 5 cents each. But high MS grade common wheat cents can sell from dollars each .. to much more ..
Now for you trading your silver coins for
Kennedy halves. Selling the coins you listed might bring you $100.
That could get you a good start on a BU Kennedy set. If you were just wanting a circulated set from roll hunting, that money might get most of all the P and D's.
You have to decide what is best for you. Some will say .. keep the silver. Some experts say silver may go as high as $50 per oz. and gold to $2000. Some say we are near the high and it could drop back down.
I do have to say, if you like modern coins, like I do, I would by mint and proof set. Start at 1964 and try to get them all to current. Once I got all or most of them, I would buy the dansco's break them all open to fill the Dansco's. And you will not only have the Halves but all the other coin sets too.
The most important thing is to take your time. Collecting coins can be a lifetime hobby. By taking your time
you will learn how to buy the best coins at the best price.
I just want to add that collecting lower grade stuff can be fun to. Putting together a set of circulated set such as wheat cents, Liberty head nickels can be done and bring a lot of joy.