As for cash flow, from sales; probably in year two and three which should match the timing for the housing market to reset past bottom of market and on to the stable appreciation side again.

I would narrow down to three companies, then bring the best quote to the two higher roofers and see if they are willing to beat the pricing.

All three.

The most relevant exceptions are the last three above in bold.Theres a lot of noise about the topic and its very confusing but the above are the actual rules atleast regarding conventional fannie/freddie financing. 

Your cleaner and your handyman should be more than sufficient if hiring smart!

I think purchasing either a three family or fourplex is the best bang for your buck.

I find that sufficient.

Others say a visual inspection is sufficient, unless there's a reason to drill, and charge between $500 - $1K per inspection.

My county is Very concerned about “occupancy and overcrowding”, so they made an ordinance that says, “A group of not more than three (3) persons not related by blood or marriage living and cooking together as a single housekeeping unit.”

Use the top three or four discriminators so applicants can screen themselves.Then you need to have clear screening criteria yourself.