It’s been a wild ride—full of challenges, lessons, and a few big wins that made it all worth it.

Bryan,This is one of the biggest challenges when investing in C/C+ areas, and it’s even more amplified in D-class neighborhoods.

Some people seem to get locked in to one place they find, or a place a friend or family member is selling without really evaluating the available market.In a small town in East Texas I would think your biggest risk is a big player coming to town that can absolutely crush a smaller player. 

While I own quite a few rental units already, I thought condos might be a good option to gift to my kids when they turn 18, offering them a safe introduction to property ownership without too much risk.However, my challenge with investment condos is that the cash flow always seems terrible.

@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?

What’s been your biggest challenge so far with the expansion?

Changing careers can certainly be a challenge, but it sounds like you're equipped with a solid foundation thanks to your sister's support.

Also would love answer to the following: - Are there any specific challenges or advantages you experienced compared to a JV structure?

Your journey into short-term rentals sounds like an exciting shift—I can feel your energy for taking on a new challenge. 

The biggest drawback I see is that you are not in control, unlike owning your rental property.