I intend on sending the tenant a bill for the exact repair cost as "additional rent" (per the lease) instead of evicting in the winter and deducting from the security deposit.

Bet they're making their car payments (walking sucks! 

Is there a way to access the additional features without creating a new Stessa account through the BiggerPockets link? 

In addition to that, the septic tank is undersized for the size of the home.

You bet.

Additionally, are there any other factors I should be considering when purchasing a duplex or triplex?

Additionally, how many calls does it typically take you to successfully close a deal using this approach?

In addition to offering "cash for keys" assure them that they can use you as a referral on their next tenant application, or offer them a short term-2 month lease.

Additional costs will creep in and costs seem to go up faster than rents, so I would sell and try to otherwise optimize the VA loan. 

In short, I can afford the additional $1100/mo cost of a second house, even until I rent it out.I have around $35K in HYSA and emergency funds that I could use for a down payment, but that's less than 20% which would be required for a conventional loan, assuming full purchase price.