I came across a duplex listing in a good school district that is also within my budget.

She is very old school, she mentioned that the seller would only contribute to the “traditional” closing costs, around 2k 

Look for parks, schools, groceries, and local hangouts—these things matter!

If you didn't, seems like a bad / inexperienced accountant to suggest such a thing.In my opinion, its the same as telling someone to go to a trade school and get a new career.A STR can help you lower your taxes but I would only do it if you were planning to purchase a STR.A STR is a business, you are responsible for furnishing the house, responding to guests, providing a great stay and experience, etc

The key then will be how to manage and save money which is not taught in schools and I can admit I was awful at saving money in my early years. 

Seller is an elderly former school teacher of mine; does have somewhere to go but will be uncomfortable for her, 2.

However, it seems like it might be too late to secure tenants for this school year.

Seasonality driven by factors like weather, school schedules, and buyer habits affects housing demand and pricing, often making certain times of the year more favorable for buying or selling.

Plenty of renters and although home to a state school the town does not feel seasonal due to the other major employers.

I think a handshake conversation goes a lot farther than a phone call (old school).