If you’re not well-versed in lease agreements, security deposit rules, or eviction procedures, you could run into trouble.❌ Emotional Stress – Handling tenant issues (especially late payments or evictions) can be stressful, especially if you live in the same building.Hiring a Property Manager in ChicagoPros of Hiring a Property Manager✅ Less Stress & Time Commitment – A property manager handles everything from finding tenants to collecting rent and coordinating repairs.

Frankly, the property manager should make a move smooth by sending all the files and transferring all the deposits in 1 statement.  

Here's a good folder setup.Bank StatementsCredit Card StatementsProperty Management StatementsMortgage StatementsSTR Platform StatementsInvoicesReceiptsClosing Documents (Purchase/Refi/Sale)LeasesCheck & Deposit ImagesVendor ContractsW-9’s & 1099’s

Sellers may struggle to mentally shift from "owner" to "tenant," which can create challenges with boundaries and property care.Security Deposit:If you’re doing a temporary leaseback, be sure to collect a substantial security deposit to cover potential damages and ensure they vacate on time.

All deposits and rents are collected through RentRedi. 

Each jurisdiction is different, but typically include a substantial deposit due same day up to full price deposited that day. 

Set up a Joint account with the seller so you can make deposits to continue the automatic payments to the lender until you refinance the property.Thanks,Dustin

Making additional payments or taking a shorter term are just depositing more into that savings account (it's not like the property appreciates more by paying down the loan). 

However, I have offered two thingsA)  Higher deposit -  this way the owner's fears are alleviated somewhatB)  Property management - offer the owner that you will essentially property manage the property for them.     

I lost another $1000 in inspection fees but should get back $2000 earnest money deposit.