All member email alias issues

I am the President of Omaha Toastmasters Club 281. Website: 281.toastmastersclubs.org. We have one member, R. Friedman, who is having issues sending and receiving emails to the group aliases. We've checked his email address multiple times on the site. We've also checked to make sure he doesn't have any filters on his email inbox and that messages aren't being sent to his spam folder. Everything appears to be in order, but he doesn't get emails. He is the VP of Education so this is kind of a problem that he can't get or send member emails. Occasionally a message goes through, but I'd put it at 19 out of 20 times it does NOT. Any insight you could provide would be helpful.

I can emails coming from and going to Friedman, I do not see any rejections. He will have to ask icloud what they are doing with his emails.

Sep 2 02:58:54 toastmastersclubs sendmail[24006]: s822wq5g024003: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:02, xdelay=00:00:02, mailer=esmtp, pri=122803, relay=mx5.mail.icloud.com. [17.172.34.68], dsn=2.0.0, stat=Sent (Ok, envelope id 0NB9002O56Y44Q40@st11p00mm-smtpin007.mac.com)
Sep 2 18:03:41 toastmastersclubs sendmail[26154]: s82I3dUa026141: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:02, xdelay=00:00:02, mailer=esmtp, pri=122143, relay=mx1.mail.icloud.com. [17.158.8.67], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBA00G29CU4AZ20@nk11p00mm-smtpin014.mac.com)
Sep 2 19:46:34 toastmastersclubs sendmail[16482]: s82JkSUM016474: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:06, xdelay=00:00:06, mailer=esmtp, pri=1300450, relay=mx3.mail.icloud.com. [17.172.34.65], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBA00CEOHLGIBM0@st11p00mm-smtpin011.mac.com)
Sep 2 22:43:58 toastmastersclubs sendmail[29755]: s82Mhuxk029749: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:02, xdelay=00:00:02, mailer=esmtp, pri=121698, relay=mx4.mail.icloud.com. [17.158.8.62], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBA008O9PT994X0@nk11p00mm-smtpin007.mac.com)
Sep 2 22:49:18 toastmastersclubs sendmail[12691]: s82MnF3n012685: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:03, xdelay=00:00:03, mailer=esmtp, pri=121629, relay=mx6.mail.icloud.com. [17.158.8.110], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBA00MCRQ24BRC0@nk11p00mm-smtpin001.mac.com)
Sep 3 01:27:48 toastmastersclubs sendmail[2573]: s831Rlcp002565: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:01, xdelay=00:00:01, mailer=esmtp, pri=125453, relay=mx4.mail.icloud.com. [17.172.34.67], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBA00KF0XEBQZN0@st11p00mm-smtpin009.mac.com)
Sep 3 01:29:21 toastmastersclubs sendmail[5623]: s831TKJG005620: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:01, xdelay=00:00:01, mailer=esmtp, pri=125871, relay=mx4.mail.icloud.com. [17.172.34.66], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBA00FOWXGWRNN0@st11p00mm-smtpin008.mac.com)
Sep 4 13:09:42 toastmastersclubs sendmail[10128]: s84D9ejD010125: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:02, xdelay=00:00:02, mailer=esmtp, pri=136735, relay=mx3.mail.icloud.com. [17.158.8.61], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBD00L0POK5V4E0@nk11p00mm-smtpin006.mac.com)
Sep 4 16:57:09 toastmastersclubs sendmail[7207]: s84Gv4Dc007202: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:05, xdelay=00:00:05, mailer=esmtp, pri=121691, relay=mx5.mail.icloud.com. [17.158.8.111], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBD00BBUZ36DDS0@nk11p00mm-smtpin011.mac.com)
Sep 4 17:05:02 toastmastersclubs sendmail[27419]: s84H4wmp027414: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:04, xdelay=00:00:04, mailer=esmtp, pri=122541, relay=mx4.mail.icloud.com. [17.172.34.67], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBD005U5ZGBHYG0@st11p00mm-smtpin011.mac.com)
Sep 4 17:10:23 toastmastersclubs sendmail[10631]: s84HANfP010631: from=<friedmanrc@icloud.com>, size=1839, class=0, nrcpts=1, msgid=, proto=ESMTP, daemon=MTA, relay=nk11p04mm-asmtpout002.mac.com [17.158.236.237]
Sep 4 17:10:38 toastmastersclubs sendmail[11133]: s84HAZNi011129: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:03, xdelay=00:00:03, mailer=esmtp, pri=122567, relay=mx2.mail.icloud.com. [17.172.34.11], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBD001GIZPNXHU0@st11p00mm-smtpin004.mac.com)
Sep 4 17:26:56 toastmastersclubs sendmail[26223]: s84HQsCE026217: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:02, xdelay=00:00:02, mailer=esmtp, pri=124059, relay=mx4.mail.icloud.com. [17.158.8.51], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBE009220GVEBA0@nk11p00mm-smtpin016.mac.com)
Sep 4 17:50:55 toastmastersclubs sendmail[30108]: s84HosMG030102: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:01, xdelay=00:00:01, mailer=esmtp, pri=125293, relay=mx5.mail.icloud.com. [17.172.34.68], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBE008NK1KUN4V0@st11p00mm-smtpin016.mac.com)
Sep 4 17:53:40 toastmastersclubs sendmail[6223]: s84Hra75006218: to=<friedmanrc@icloud.com>, ctladdr= (501/502), delay=00:00:04, xdelay=00:00:04, mailer=esmtp, pri=136541, relay=mx1.mail.icloud.com. [17.158.8.68], dsn=2.0.0, stat=Sent (Ok, envelope id 0NBE00HX91PDY1K0@nk11p00mm-smtpin009.mac.com)