One is a fourplex and the other is a duplex with a single family home on the same lot.What are my options and what would you do if you were in my shoes?

It's called a 1031 exchange which refers to Section 1031 of the IRC which states: “No gain or loss shall be recognized on the exchange of property held for productive use in a trade or business or for investment, if such property is exchanged solely for property of like-kind which is to be held either for productive use in a trade or business or for investment.”To be clear, there is a process and time limits on when benchmarks need to be accomplished to qualify.

My sole proprietorship company manages all of my rentals, so yes, in essence I self-manage.  

And if so should they be sole member LLCs with just the owner or can they include both of us?

On the flip side,  having 10-20 postings of virtually identical content only clogs search results when the sole difference is a timestamp.Keeping a topical organization is really important when REI is such a B I G subject.

No one who's ever spent their first 10 or 20 grand hasn't been in the same jittery shoes. 

Malibu, CA joining the frey on STRs:A very typical response to STRs ( according to patch.com) is The Council is concerned that people would buy property in Malibu for the sole purpose of renting it out on services such as AirBnB.

@Austin DeardorffWhat's up Austin...I remember being in your shoes.

It's helpful to look for an attorney who has a high level of empathy, who can put themselves in your shoes, knows exactly what you're going to be worried about before you're worried about it, and counsels you on how to proceed.

Going forward once i start signing agents on, how do i want to structure my llc ( s corp c corp or sole proprietor ).Also if i plan to do property management is it okay if that money commingles with my agent commission splits?