That the majority of the owners are paid up.

If the second property you are buying is not turnkey, will require some work, and there is a clear value/range of what you can bring the property to by adding value then you can refinance to pay back the majority if not all of your HELOC (used for downpayment or to buy the property completely).You'll need to know how to analyze an after repair value of the property to figure out if that technique can work or not.

The tenant is paying their portion of the rent (the majority is coming from city) but the tenant has been difficult to deal with and I'd like to find an new tenant once their lease is up.

We continue to see the majority of sellers offering partial or full compensation of buyer agents.

Like others have said, you don't need an LLC to get started with STRs.If you own a single unit or even 2 or 3, simply make sure you have the best insurance to cover any issues as well as an umbrella that can cover any excesses.Plus the major key will be maintenance.

For example, let's say there was a major development on rent control, that would allow me to pivot and understand next steps.

I think one of the major issues is W valley basically only has Pinot .. compared to Napa Sonoma were virtually all varietals are grown and bottled. 

Case in point, in 2017-2019 while facing a severe housing shortage, Minneapolis enacted its 2040 Plan, becoming, “the first major U.S. city to end single-family exclusive zoning, opening the door for developers to build multifamily buildings on lots where a single-family home used to be (NBC).”

DSCR sitting mid 6s today in the majority of scenarios. 

Is it OK for the operating company to claim depreciation for the properties that are owned by the holding company.This situation could cause major passive loss issues depending on your situation.Scott Smith has refused to weigh in on this “difference” and has since referred me to a CPA who is so busy that I won’t be able to speak to him on the phone until May.