I'm an independent agent here in AR and I write a lot of rental property, with ~6 preferred markets and if the properties have some issues, age, claim history etc.

As it relates to lease end dates I've seen two things work here. 1) You can stagger end dates as mentioned above or 2) you can optimize for summer - this works better for us in areas where you see students or families with school age children moving to align with the summmer months.Separately, this is a great argument against month-to-month leases.  

@Jonathan GreeneWe are looking to continue to grow.

You could grow a portfolio but will it be sustainable?

Central Florida is a solid market with strong rental demand, especially in growing areas like Orlando, Tampa, and Lakeland.Focus on building relationships with local agents, lenders, and property managers—they’ll help you identify good deals.

The midwest is not growing as fast as the south and southeast.

After exiting that business, I began exploring innovative solutions to the growing senior housing crisis.

Many others on here have said the same thing, but at your age i'd focus on career.

My son (age 24) however, is an independant contractor / self employed and is trying to buy a house. 

I recently read in Forbes that investing near growing transit hubs can offer great appreciation potential.