I’d love to hear from fellow self-managing landlords about the biggest lessons you’ve learned along the way—whether it’s handling difficult move outs, maintenance strategies, or unique ways to streamline day-to-day operations.

One of the biggest time sucks can be finding & screening a tenant!

If they try to pay their labor as 1099 they run at great risk of violating a host of draconian labor laws such as AB5, the borello law and a litany of "misclassification" laws.There are substantial differences in how "right to work" statstate as operate as opposed to "non right to work" states.SBA defines a small business based on employees and revenue size.

By consolidating and repurposing these spaces, property owners can unlock additional revenue streams.Upgrading Amenities.

@Mattin Hosh first, most cities in Metro Detroit have some type of rental property inspection every 2-3 years.It's not really a big deal 99% of the time - especially for owners who are NOT slumlords:)Also, a quick Google search will show that several states/cities are passing/considering similar legislation.One of the biggest mistakes we see newer investors making is NOT properly understanding Neighborhood/Property/Tenant Classes and naively assuming that any rental they buy will deliver Class A results.Read our copy & paste thoughts below and DM us if you'd like to dicuss more about the Detroit market:)-------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Realtor.com was the 98th most used website in the U.S. in 2015. 18,069 different websites link to Realtor.com.When Advertising on Zillow you should focus your attention on getting the biggest market share you can afford in one zip code.

Biggest issue.

or “What has been the biggest challenge for you as a new investor?”)

I would just take into account that a lower down payment will mean a higher monthly payment so be sure to run the numbers conservatively in order to ensure your STR revenue is able to carry your monthly payment with this higher mortgage cost. 

With that being said, the interest rate is going to be the single biggest determining factor for whether you're barely breaking even, or seeing a decent monthly cash flow.