I'm looking for help choosing a market to work and invest in.

I don't think you need to choose because you can easily pivot from one to the other.

When choosing a city or neighborhood for investment, it’s crucial to consider:Economic drivers: Look for areas with diverse and growing job markets.Population growth: Areas with increasing population tend to have higher demand for housing.Rental yields: Compare the average rent to property prices to gauge potential cash flow.Future developments: Infrastructure projects and new developments can boost property values.Additionally, it's vital to get local insights.

You mention multiple states in your title, such as Indiana and Illinois.When choosing a professional, make sure they understand multi-state taxation in addition to real estate taxation.

Since you are new, if you choose to do a STR, I would recommend hiring a great property manager who can do it for you.  

As the landlord's business grows they can choose to not renew the tenant's lease.

I choose condo's for this market because it's no exterior upkeep and provides pool, gym, tennis etc.

Is there a resource to send a tenant for screening early on, so that they can use it as a PTSR if they choose not to lease with us or are not approved etc?

But in your case, since that is also one of the higher balance loans, I might instead choose to focus on the lowest balance first, that being the 4.5% at $375K.

In a reality where more and more people are choosing to have no children, it's overkill.But you have it now, so today your conundrum is how to move forward from here.