I read that rate as paying an extra month and half worth of your annual rent collection to buy income insurance for the year.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

.- You're right, if you want to maximize your first priority (positive ROI), you'll usually benefit more by finding an underpriced rehab on or off market and then developing it with an ADU and/or DADU.

Here are a couple of ideas that might help:1031 Exchange: This is usually for investment properties, not your primary home.

Usually after walking through the property he is able to give me a good ball park figure of what the renovation should cost barring unforeseen issues.

There's a lot to it and many people set it up and then don't want to do all the extra steps. 

Usually the minimum loan amounts are higher compared to a 1-4 program with a loan minimum often of $400K.

HELOC: they are out there, but you typically have to hold title in your name and not under an entity. 70% LTV is usually the cap, and rates are double digits (mid teens).

Corporate travel, divorce, etc. are other potential tenants.If costs in your market allow, I would encourage a duplex purchase vs SF...potentially 2 income streams vs 1 would help offset the extra cost of a duplex.  

There aren’t many awful neighborhoods, but if you hear anyone talking big cashflow it’s usually a D/c- type neighborhood, though there are still a few places with decent opportunities.