I used free tools like Zillow and Redfin to come up with a home value, asked him some questions about the condition of the home, made him an offer, and he accepted it.

That unit with the waitlist is the only pet-friendly home (duplex) with a fully fenced-in yard accepting more than 1 pet, including larger animals. 

Just because someone has a voucher doesn't guarantee we will accept them. 

@Rafael Valdor some advice when screening PMCs-----------------------------------------------------------------------------------------------------Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

The following day I got a small counter back and I accepted.

True, I am 100% with you on that.The point here is, when you analyze, you do based on what you know now (what is known as a fact today) and on what is highly likely to happened (again from today) and to accept the fact that things might change tommrow.Life happened every day, that’s why  we need to stay firm with our direction but flexible with our approach.having lived through the HORRORS of those years fully engrossed in the industry almost nationwide... it was regional on who did well and who had troubles.. no question well positioned landlords in Portland for instance no issue.. 

Now that people are starting to socialize again and this city is opening back up soon, I would imagine that many renters and visitors will be coming back to SF in the next year or two.

His roadmap for retirement is $500k liquid assets, paid off primary home, and more than 1 income source (real estate, part time job, social security if old enough, etc.).

Because only motivated sellers are willing to accept an offer below market value.

Quote from @Michael Smythe: Besides MANY self-labeled "gurus" exaggerating their success, many of them just supply readily available info.If you're too busy to find the info and are willing to pay for it, no problem as you accept their time vs money solution.REGARDING S8 GURU ISSUES SPECIFICALLYMost of them don't share all the facts about how Section 8 actually works.They claim you can get HIGHER rent from S8 tenants vs private-paying tenants.Why would the government allow our tax dollars to be spent this way?