I didn't read all responses so I'm sorry if duplicated.
We just went through our estate docs for the 3rd time....we are 57/61. We struggled with many of the same things. My pieces of advice are:
1) In the will just make the bequest...i.e. "I bequest my musclecar to Joe" or "I bequest my wedding ring to Phyllis". Then, you can have a separate letter that is not part of the actual will that your executor will have access to that can "explain" things more. For example, it might say "Joe, you helped me work on that car every weekend for 2 years, and I appreciated that. I want you to have it. But if you don't have room to store it or money to insure it, just sell it or do what you want with it."
2) Make some sort of allowance for pets. We have a Sheltie and no family who likes dogs. We found a person who rescues Sheltie's and got verbal agreement he would take her. We put his info in the will, and bequeathed him a few thousand dollars for care for the animal.
3) Put as much property as you can into beneficiary status...as beneficiaries take precedence over dispositions in a will and make it easier for everyone. This is mostly your bank accounts, IRAs, etc.
4) Leave many other documents for your executor.
a) list of passwords to key accounts/websites.
b) Locations of key documents...do you have a PO box? Safe combination? Etc.
c) Funeral instructions
d) List of accounts (we used an Excel spreadsheet) showing balances as of xx/xx/xx,
contact names for each company, account numbers, etc.
e) If you own any businesses, make sure your operating agreement spells out what
to do in the event of your death. I own rental properties in an LLC...and I want
my wife to be able to make decisions such as sell them should I die...so I put this
in the operating agreement.
f) Obituary
g) Key contacts (who do you want to know that you've died?)
I'm sure I forgot a few, but you get the idea. Our info is all in a binder that has a clear label stating "If I die" on the spine, and I showed my executor (my brother) where it's at so he can easily find it. Of course I also gave my brother a copy. My physician has a copy of our health care proxies also. Make sure you list who has your documents so that when you update them 10 years from now you can collect them from anyone...avoid wrong copies floating around.
Good luck and thank goodness you are doing this now....it has given us tremendous peace of mind.