This experience proves that even with challenges, strategic renovations and persistence can lead to a profitable outcome.

I suspect maybe something like Hagerstown or Cumberland, which yeah are Class D like markets with declining populations, high drug problems, no strong job base which leads to non paying tenants.

If R5 is an option, then I might have some areas I could look into.All of this leads to my two questions:1. any tips/advice on how to best transition between my current primary residence and a new one?

Can you imagine calling hundreds of leads a day for "investments" and seeing all those who keep track of the dollars you're raising exit in tandem?

He told me that without installing a sump pump system (at a cost of $12k), the foundation will continue to deteriorate, which could eventually lead to bowing basement walls—an issue that could cost upwards of $50k to fix.The inspector asked if the previous homeowner disclosed any water damage.

The conversation may lead to some form of "Would you mind if I replace it?"

The best way is with people you know. 

Due-on-Sale Clause If transfer taxes are not a concern, the next consideration is the due-on-sale clause, which could lead to loan acceleration.

Just curious why people think they should be in jail?

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.