As Rob continues to weather the storm, it's clear his strength are weddings. Maybe consider adding "anniversary" packages to offerings.  People who are celebrating milestones like 25 years, 30, 40 plus can do with some new portraits.  Recent news events indicate tons of Canadian snow birds who are in Florida might be stranded temporarily.  Some are choosing to extend their stay instead of deal with new federally regulated travel restrictions.  These snowbirds might appreciate having something fun to do like a photo shoot.  Professionally shot images will be good for everyone's social media accounts.  
With all Rob's experience and contacts for designing packages, he should be able to modify what he already has and come up with something new to serve the needs of older clients with money.  He can up-sell with offering to ship printed products to Canada.  
Obviously a season of large weddings are best for Rob but this idea can help weather the storm.  Once gatherings are happening again, this idea can be used during quieter months.   
Best of luck.