First, an S Corp, or any tax entity for that matter does not allow you to convert personal expenses to business expenses.Second, if you buy a property under an S Corp, and rent it to yourself as a personal residence, that transaction will not be respected for federal income tax purposes. 

Having a chat with a planner in your respective district would add a little prospective.

Hi, if a landlord wants reliable and respectful tenants that pay rent on time, what features should that landlord's rental place offer that tenants look for? 

Value and respect everyone's opinion.

Assuming I can keep it rented at that price, that equates to a respectable 11% cash-on-cash return per year.

Check your state guidelines with respect to evictions as they are mandated at the state level.  

I respect and love teaching but I need to find something new. 

if the tenant is good and takes care of the property well - be flexible with them. these are the tannates you need to respect and as long as they catchup you are good.

I tell you this with the utmost respect for your hustle.

Also a big fear I have is that when I do reach someone willing to sell me an off market property how can I be sure not to pay too much all while respecting the seller and not offering so little that I never complete a deal?