We also have a weekly newsletter for STRs here called BiggerStays that you can sign up for free in your profile settings! 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

There’s no single right answer to every situation, but the more you educate yourself and build your network, the more confident you'll become.Lastly, don’t hesitate to ask questions here, no matter how small they seem.

I've begun cold calling and looking to alternate methods of finding deals, but if anyone has any advice for overcoming this I'd love to connect.

Call it nicely it’s market inefficiency but recognize that Chicago historically is a very segregated city.  

Back in 2022, we tackled a property we affectionately called the "Scary House," and trust me, it lived up to the name.

That's cool.

Hi Benjamin, call three insurance companies and get a quote, start there first.

Curious why any tax pro would argue with that.If filing state tax returns did not take any time or money, then there is no harm in filing them.

Line Item Fee Collected Rents 10% of All Collected Rents New Tenant Search & Onboarding $500 Business Hour Service Calls $80/hour + Materials Cost + Tax After Hour Service Calls $110/hour + Materials Cost + Tax HVAC Cleaning & InspectionGutter CleaningSpring/Fall Exterior CleanupSeasonal Mowing & Weed TrimmingSeasonal Snow PlowingGeneral Contractor Vendor Cost + 10% Oversight Fee