Looked up some services that hand address the envelopes but it's expensive. $0.75 an envelope so $750 for 1000. Yikes!

Researching companies that can print them and it looks hand-addressed. And pricing a Task Rabbit person as well. 

whitney.zelig@gmail.com
https://www.letterprinting.net/store/pc/Hand-Addressed-envelopes-d21.htm
this place will print envelopes with fonts that look handwritten. I called and their estimate for 1000 envelopes was $94.01 plus $17.64 in shipping so total $111.65. Price includes envelopes and printing.

Link to types of fonts to choose from

Chris  

i personally like #10

we can also pay for the postage and have them stamp the envelopes if we didn't buy the stamps yet. 

That sounds kind of lovely.

So they would print out the names, use postage, and print out the letter that goes inside? for how much? Vania  

Yes, they could do the whole process. I'll get a quote. I told them we were stuffing the envelopes because there's a $2 we're putting inside, right?

Look into some options as well where they stuff the envelopes. Did someone get annette the printed off list so she can start addressing the list. I want to send these out every six weeks and we need to hustle and get a system in place

Staples charges $152.99 for 1000 security, peal & seal envelopes with addresses printed on them. 

Chris  

ok whitney.zelig@gmail.com this is the closest Staples to your house, about 10 miles away.
Staples, East University Pkwy
336 East University Pkwy

Here is a couple of handwritten fonts I downloaded for the addresses.
Tell me which one you like. i think 4 or 5 are pretty good. I will create the file and have Staplse print a test envelope for you to pick up. 

Handwritten Fonts for Envelopes.pages 142 KB • Download

the document isnt loading fonts for me-

please screenshot- you can download  amazing screen shot extention

i vote 3 i think