Hi, I noticed there was new casita/ADU laws that went into effect in Jan 2025.

.- I would highly suggest you plan on using a property management company.

So advice to get the house against him and he will move out on his own is HIGHLY unlikely.  

However while people in Windsor doesn't have the luxury of high paying jobs that GTA residents have, is it just a temporary fever of buying houses, or there is really something going on in this city ? 

As inflation drives rent growth, properties in stable markets like the Midwest can continue to deliver returns even in higher-rate environments.Market Conditions Favor Real Estate RecoveryThe commercial real estate (CRE) market has faced significant challenges in recent years, but signs point to a recovery:Bottom of the Market Cycle: CRE appears to have reached its low point in late 2024, with 2025 marking the start of a slow recovery phase.Limited New Supply: High interest rates have curtailed new construction, which should drive rent growth in the coming years.Policy Changes on the Horizon: There is growing discussion about potential policy shifts under the new administration, including a return of 100% bonus depreciation and lower interest rates.

For example, maybe you will get to 10, 20, 30 houses and then find an owner who has a large portfolio and all of a sudden you are at a high door count and now need to hire, need to build your policy binder, and all the other stuff that comes with running a business.

Talk to your attorney, and if you dont have one, get one - as @Ken M. said, this is highly specific to the state and the circumstances.

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.

IT's the worst place in the world to be a landlord and very high risk.

The Retainer Fee is credited towards whatever they buy from us in the 90 days, so in effect, costs them nothing.Note: we're not doing this to make money, but to avoid the time-wasters.