Hi Kailas - Yes, you can typically rent out the main house and the ADU to separate tenants on separate leases (so long as you're compliant with city regulations/restrictions).

I got a good deal on the house, but do not want to invest in it if I would be out of compliance with renting regulations.

ONE window that will stay up on its own in each room, no holes in flooring (oddly strict on this one, even a dime size tear in a floor is considered a tripping hazard) a light in every bedroom and enough room for a twin bed and a dresser.

Its seems many pros are burying their heads to the regulations or not thoroughly understanding how to interpret STRs in the tax code (the transient rental rules etc).

So it isn't a complete waste, you would simply need to follow the strict reading of the law with no private clauses for consideration...I'm not sure how that plays out since technically if the lease is void, so is the tenancy meaning you could terminate anytime and not wait for the original lease expiration...I'm sure that's covered somewhere, but again I'd ask my local atty what to do given this is such a locally specific issue. 

I loved being a landlord and felt good about it, but since its gotten to be so regulated and anti- landlord here, its best I get out.

The last house I bought, was brought to me off-market by my agent, and it's seeming that off-market is the only way to get good properties without the MLS prices.I've recently got a nice business card printed up, and would like to start a direct mailer campaign, using BatchLeads to find multifamily properties in the local towns that I wish to invest in.I have a pretty strict criteria about what I'm looking to purchase at this time:-Legal 2-or-more unit large Multifamily (not required to be owner occupied)-Each unit should be at least 3 bedrooms (so if it's a duplex, it needs to be 6+ bedrooms)-Sewer (not septic)-Gas (not oil)A lot of this information is not readily available online, so once I start my mailers, I'm sure I'm going to find people who eventually respond, but that don't have criteria which match what I'm looking for.I feel like it would be a waste if I paid a bunch of money for direct mailers, and then someone reaches out to me to sell, but their house doesn't match the criteria of what I'm looking for -- I don't know anything about wholesaling.What can I do to monetize these leads, or is the answer is that I need to learn So we believe no lead is a bad lead.

You're absolutely right—some investors still flock to cities like New York and San Francisco, even though these places come with more tenant-friendly regulations.

If you manage homes built before 1978, there's a key regulation to be aware of: the Environmental Protection Agency (EPA) requires property managers and Landlords Nationwide to be certified in lead-based paint handling.

Per fair housing regulations, I can't answer this question.