Was it finding the right market, navigating local regulations, or building a network?

Make sure you have an appropriate buffer and expect to be over budget.

You have to screen the company to verify they hold the appropriate licenses, insurance, etc.

Short-term rentals would be a solution, but due to strict short-term rental laws in rent-controlled areas of Los Angeles, options like Airbnb are typically not feasible.At present, I have a $5 million property in Encino with two units that we cannot rent out short-term due to rent control regulations, and the numbers don’t work for a long-term rental either.

-Have enough room in the back of the lot to add a new duplex (zoned appropriately, etc).

If you buy in the proper STR areas there is practically zero regulation risk. 

Legal ConsiderationsZoning & Regulations: Make sure the property is zoned for a duplex and complies with local regulations.

@Lena CastellanoTo prepare for your first real estate purchase next year, explore house hacking options, research rental regulations, network with contractors and investors, practice deal analysis, join local REI groups, and connect with agents.

There's a very good chance the issue(s) you face have already been discussed and answered.Ask questions in the appropriate forum.

There are pros and cons to long term and short term from a rental management side, and purchase/acquisition.Long term = lower vacancy, lower expenses, potentially lower revenueShort Term = higher vacancy, higher expenses, potential for higher revenue, financing is more expensive than long term rentalsWatch out for local STR regulations, they vary from city to city.