I.e. a property sold down the street with 1 extra bathroom and 250sf more.

Do you have a specific area/neighborhood of the city where you are looking to househack? 

No one wants to kick a senior citizen out on the street.

I agree with Alecia-I would start with something smaller, find an city/area of town you like. 

If your goal is to offset your mortgage with a house hack then Lowell would be a good bet, but if you're looking for a longer term appreciation play then the areas closer to the city would be better, although the offset from cashflow may be lower than what you're looking for.A good step for you would be to dig into specific areas more as @Lien Vuong noted above.

Ok, well now STRs are regulated in that city, and that same income approached value plummets since the home can only be rented as an LTR.

In cities with static or declining populations, the existing housing supply typically meets housing demand.

For your question, as far as I understand, the city of Binghamton doesn't allow STRs, but a lot of people do them anyway.

Well, I heard about this tactic, and was so excited to try it out until I tried looking through Jackson County’s public records portal here in Kansas City.

Its not near any major cities where someone might look at it as a long play for path of progress.Another option might be to see if a solar farm or wind farm company might be interested once its clear cut.