My professional background is data science / analytics, which means analyzing cash flows will probably come more naturally than building relationships, which apparently, is how one finds deals worth making.Are there meetups in these areas I should attend (digitally at first, presumably)? 

I know this is above and beyond what most municipalities require, but being fair will make the whole process easier.Additionally, a new landlord can reduce the 60-90-day notice by offering more moving assistance (cash and/or labor) if they move sooner rather than later.

Give it a read, and you'll have a fair understanding of the process. 

For first flips better to start with a  small cosmetic rehab  until you get to know the process and the team well.

Quote from @Daniel Windingstad: Quote from @Obed Calixte: Some people have the personality, processes and systems & time to self manage, some do not.

Emphasize how this arrangement could work to their benefit, offering steady income, avoiding a traditional sale process, and giving them the freedom to move forward with their plans such as buying that sailboat and sailing around the world.If they ultimately decide they’re not interested in selling, you’re still in a great position to continue your search and buy your own property in the near future.

Can someone walk me through the thought process I should be using when constructing the offer?

Offering a streamlined process, no repairs or renovations prior to selling, no market costs or agents fees for my family member, in return I will gain invaluable experience in the market and in the field along with providing my family with wholesale services.

You'll typically need to set up your account and get familiar with the process of working with the local housing authority.

It’s an interesting approach, but ensuring a strong screening process and a legally solid agreement is key.