In hindsight, perhaps this is not the best profession to be in when it comes to passive income (although I do receive "residual" checks for some productions... so there is some passive income involved).At this point, it looks like my most feasible path to $5K/month passive income would be to scale a RE portfolio, and have some diversification in my investments as well.

And then you need to HOPE you sent the right marketing piece to them, and HOPE you filtered that list correctly, and then go to all the hassles of skip tracing and then RESEND those letters again spending an other residual fortune? 

People attribute a lot of what we do to luck, being in the right place at the time, or just happenstance - this is because they fail to see the hours and hours of studying, exploring, and experience that has brought us to our successes.As Branch Rickey once said "luck is the residue of design." 

Since nobody else has said this yet I'll be that guy:  It depends on your goals.Flipping the house will get you more profit sooner, but it'll be taxed at a higher rate but it'll be liquid in a few months.Holding the property get you the long-term residual cashflow and you'll get most if not all of your starting capital back, But it'll take longer to see your profit.So to answer your question with a question...Are you looking for quick profit (sweet vacation, replace career, etc.), or are you looking for steady long-term income?

“It would have a big impact,” he said, “like Volkswagen had for Chattanooga, which created 3,000 employees and about 8,000 residual jobs in that area.

Know what to look for in terms of evidence.... drug paraphernalia, odors, residue on walls and in furnace filters, etc.What did they say when you served them the prior notices to comply?

is there an initial buy in, a one off payment, or residual monthly fees?

Flipping houses will almost always bring more short term cash but it is nice to have enough residual to cover your living expenses and then flip for the extras.

I will eventually build my residual base but factoring for inflation, the retirement goal may not be attainable. 

If you only need 6 or 8 place settings per property, you can use the residuals at another property, or keep the extras to replenish the lost/stolen/broken ones that will definitely come with a rental property.At restaurant supply stores, the little knick knack types of items are usually about the same price you'd pay at Target, but less than you'd pay at say, Williams Sonoma.I'd definitely say the best linens and duvet/bedspreads/pillows and mattresses you can afford, the better.