I email all my documents as pdfs with password protection, then I text the passwords to the person receiving them. 

I work for a building materials company now and took their online game from Zero to very engaged in the past few years and it's been really fun.

Overall I would personally consider how I can still grow with the freedom that I have focusing on my real estate.

The more people living in a building, the less personal responsibility each tenant feels.

Way to get in the game!

Flipping is a poor man's game. 

Do you all have any in-person meet ups?

Quote from @Dereck Olson: Hi Nicholas,  Just a thought from the possible tenant's perspective, but filling out a prequalification form and/or providing personal information before they have even seen a place and know if they will be interested in living in the property might be a bit too much to ask. 

It sounds like you’ve got a solid foundation and a smart game plan, especially with the house hacking strategy.

Once I had the right person to speak with, things went much better, and I hope that is the case for your situation, too.