It's difficult to see how a tenant will be after screened and signing a lease.

There are plenty of entry roles from cold calling, scrubbing data and find deals for investors, leasing assistant, work on construction sites, office admin, project coordinator, Title assistant, RE photographer, transaction coordinator.. on and on. 

If not, I'm guessing it would be treated as a traditional rental loan, either conventional or DSCR, using market rents rather than the rent in the lease agreement.

Unless I'm mistaken, the contract between owner/landlord and PadSplit doesn't have a defined monthly rent but a target/goal of monthly income (so it's hard to use that as lease).

For example, what would the cash flow be like after you renovate and lease out at the new rates?

I use Buildium for tracking rent, fees, leases, and collecting online payments, but I don't use their reports for much, as I end up copying my online banking each year into spreadsheets.I've been using Rental Hero for the last hour and already impressed with it.

triple end lease.

We work with an agent who specializes in leases and let her know of the properties we have available for MTR and she brings in a few reservations every year. 

• How do leases typically handle furniture/appliance damage or wear?

My advice would be, if you truly want to learn the business, lease it up, refinance, pull some money out, and go on to the next one.