I want to get at least one passive income generator under my belt and then do a few flips for some active income. - my questions are: where do I start?

Have an idea of the limits you want quoted     - Building - cost to rebuild    - Contents: do you have any business property there (appliances that are not built-in,         maintenance equiptment, furnishings in common areas) - what is the cost to replace them    - Business Income:  What is the total rents minus the costs that don't continue    - Liability:  What limit are you looking for2.

Check out the IRS own guidance for dealing with these questions:  Passive Activity Losses

So, the losses will be carried over year over year as Passive Allowed Losses (PAL).  

You could passively invest a portion of that money and make 10%+ in the stock market.

I'm hoping to find about 15-20 single-family cashflow deals over the next few years to replace my current income and bridge to retirement within 5 years.

We know all the gurus tell us that we do, right before they pitch us their course or services, but is that just them diversifying their income?

If free and clear should also consider a DSCR loan 30 year fixed no income no doc 

❌ Previous Rent: $1,100✅ Post Reno Rent: $2,000 (plus utilities)Original Underwriting: $1,900$900 monthly rent increase$10,800 additional income per year (excluding utilities)We spent $35,000 for a premium level renovation.= 30.8% return on investment (ROI)We target an ROI between 25% - 35%.

Whereas any income you get from lending your money would be taxed as ordinary income.