However, I should note that this tenant has been late paying rent several times recently, which has added some strain to the landlord-tenant relationship.How would you approach this situation?

Hey everyone,As 2024 comes to a close, I wanted to share my experience managing a 3-flat in the Ravenswood neighborhood of Chicago during my first year as a landlord.

You want to judge every single landlord in the country.

This simply means you have language in your lease that states the landlord is responsible for paying utilities up to a certain $ amount (let's say $100 for the sake of argument).

I see landlords lose thousands, even tens of thousands, making rookie mistakes that they could have avoided with a little education up front.Once the first property is under contract, start again for the second.

Yes, #1 isn't exactly true, but it makes a point that not every landlord and rental can expect to get an A/B class tenant.

We have a 14-page management contract that we've added our real experiences to over the years, with the intent of protecting both us AND the landlord.

If anything there might be a discount b/c there are so many landlords who want this option so that they don't have long term tenants in the building so they have the option to sell the place vacant.

There are several things to fear money loss on a bad investment, government involvement in RE, bad tenants that cost time and money, hidden maintenance issues and/or land issues and the list can go on.Today, I don't fear money loss or tenants,  the big unknown is how much the government wants to get involved in either taxes or landlord/tenant issues.

Common advice I've received from other landlords is to avoid them because they often leak or fail and are difficult to maintain.