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

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.

Plus, they often have established connections with handymen and contractors, making maintenance and repairs seamless.

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

Hey John,Sounds like the answer would be to utilize a DSCR lender that utilizes either pre-established STR rental income (if you can prove with AirBNB/VRBO statements) or a few that are still UW with AirDNA or a similar STR income projection program.I am aware of a few still doing it at this time, and if you can show that you know what you are doing you shouldn't see much of a cut in LTV if at all.Happy to connect and see if we can help.Good luck!

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

When I established my investor services business in 2005, I posed a similar question to numerous experienced property managers.

@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.

Once you become more established, have a large net worth, etc. you may want to consider more sophisticated trusts that can cost you up to $45,000.

Eliminate debt, establish a budget, and save.