Living with your tenants can be very challenging speaking from experience. 

Reliable, thorough housecleaning services can be challenging to find.

. • Documentaries: Check out The Queen of Versailles for insights into the challenges of hotel investments. • Podcasts: The BiggerPockets Commercial Real Estate Podcast has episodes on niche asset classes, including hotels. 

Every property comes with its own characteristics and challenges. we have sold to hundreds of investors by now and there are some that had a bad experience as far as the property goes but theres also tons who havent had any issues.

Quote from @Michael Challenger: I have no qualms with hard money lending, but I need to learn more about the process and structure to these for typical deals so that I am more comfortable and in a position to reduce my personal risk and risk to investors as much as possible.

Getting one property and cashflowing it will be a challenge. you can try seller financing but you are still going to be highly levered which just enhances the risk that you are taking on.The best way to grow is to focus on managing your rental, saving money through your W2 and crushing that - if you are a realtor you will make more crushing it as being a realtor than over leveraging real estate - then save for down payment and buy slowly. its not a rush.

My challenge is that I don't know when exactly I will be able to obtain the STR permit from the city, so I don't want to convert guests too prematurely. 

What’s your biggest challenge so far in analyzing those deals?

.: Hi there,I have an investment property in Atlanta and over the past year, the property had major challenges due to squatters.

@Blake McWilliams This is a most challenging problem with both residential and commercial investors.