You typically need to be in the $400-450k range to see those rents.

There are approximately 28 Multi-family duplexes active on the MLS ranging in prices as low as $50,000-$219,000 with a median rent of about $929.

The market still has relatively low entry points compared to other major cities, making it possible to find multifamily properties like duplexes and triplexes in the price range you’re targeting.

Typically this takes 6–9 months, including 2–3 months for permitting and 4–6 months for construction.You can browse their current plans online, with design costs ranging from a few hundred to close to $2,000: ADU Fast Track Plans2.

With interest rates on your current properties in the range a stock market portfolio might return paying off the mortgages could be a good option so you maximize cash flow.

However, the LTV that you will be allowed to borrower will be less, in the 60-70% range max.

The flat fee buyer agency fee reduces the amount of the buyer credit/refund, generally by $6,000 (although options range from $999 to $8999, depending on how much help the buyer wants from the agent).

Providing relocation assistance to tenants, for example, if I want to sell the property or move back in - this can range from one month's rent to thousands of dollars (e.g tenant has a disability, minor children, elderly it will cost you more), depending on the city.

Typical cost for the setup would be in the $15,000 range which would include production of the Private Placement Memorandum, Subscription Agreement, and Operating Agreement, Investor Qualification Forms, as well as filing Form D with the SEC, and state “Blue Sky” filings in those states where your investors reside. 

I'm 100% overseas now and no longer feel bound to invest in the city I live in.