My kids are pretty settled in their schools and it would be hard to uproot them.

Look at crime rates, school quality, vacancy rates, and rental demand in those areas.Talk to Local Real Estate Professionals: Connect with real estate agents, property managers, and other investors who are active in the specific areas you're considering.

Really if I could sign a group up for 2025 I would be very happy with that and would just try my best to do month to month until the new school year. 

@Bryon Andrews was spot on in his advice too - do some Zillow and FB Marketplace surfing every few weeks to see what rents in the blocks near your property have been renting for recently, and track how those fluctuate over time for a few months.  

I think the winter market concerns are really primarily only really worrying if you are looking at a larger SFR attracting families to due the "school year" issue - but other types of strategies I don't think its as much of a concern

Since he doesn't seem to have been able to acquire that sense through the school of hard knocks, he's not going to acquire it through sweet reason spoken to him out of his landlord's mouth."

I like the idea of diversification of my investments and I love the strategy BAM has articulated: the focus on properties with below market rents in growing areas with jobs and good schools. 

Misinformation stating that the guru dropped out of school, was fired from his job, failed in his business startup, but when he discovered” the “secret” of real estate investing, met with almost instantaneous success7.

Quote from @Craig Sparling: I consider myself an old school fundamentals guys. 

Fit buy box of A or B rated school that will appreciate over time.