This just reaffirms the power of the BP community. 

To buy a BIG property today, you will need to take on extreme leverage, make a big bet, convince mulitple other people to hand you hundreds of thousands or millions of dollars, and then you have to be right, inside of a 3-5 year timebox, about your projections, supply, demand, expenses, and cap rates. 

If the rental market is extremely profitable, you dont need more incentives to buy rentals, you were going to do it regardless. 

I am extremely handy with a vast collection of tools so can perform improvements myself.

Finding a lender in 2nd position on an investment property is extremely difficult in todays climate.

I wanted to use the free "rehab estimate sheet" but it prints out with an extremely small font and gray instead of black.

By best, I mean someone who works with out of country investors, knows the area extremely well and is well connected to local people - property managers, plumbers, handyman, etc.I'd love to connect and here how your search goes!

Short of specific decisions or clear law, the distinctions seem extremely vague, arbitrary, and a bit scary.

Salesforce is a great product and is extremely malleable to cater to what you are going for.  

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.