I strongly recommend getting involved with your local REI meetup groups so you can work out your pitch with help from other landlords.I hope this doesn't come off the wrong way without tone or facial expressions behind it. 

Quote from @Logan Barwick: I Am looking at getting involved in rental properties and debating on which option would be best.

With new regulations in Canada like the flipping tax and property gains tax, I want to be mindful of the risks involved. 

@Kiryl Ulanovich,You're on the right track:Get Pre-Approval from Hard Money Lender – Know your terms and limits upfront.Find a Deal Through a Wholesaler – Verify numbers and ensure it meets your criteria.Review the Assignment of Contract – Confirm terms, earnest money, and contingencies.Conduct Due Diligence – This includes an inspection (if allowed), verifying ARV, and rehab estimates.Submit to Hard Money Lender for Final Approval – Lender will review title, contract, and property condition.Title Search & Clear Any Issues – Ensure a clean title before closing.Close Through Title Company – Finalize funding and take ownership.Consider also lining up contractors early for a smooth transition into renovations.

.✅ 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.

Some may want to leave without the responsibility of cleaning.

At AHP, we sometimes see clean out estimates of $3,000 - 4,000 and know well that a local investor could probably get the work done for $500.                                                                                                                                                                                                  

Clean water, air, peace and sunshine are nature's remedies and in over-abundance on the Oregon Coast. 

I am able to do majority of the work involved and have been in trades for over ten years.

That will probably be your best bet, to buy a fixer and get it cleaned up and then rent it out.Best wishes and good luck with your endeavors.