But that makes some people uncomfortable.

Routine inspections from property management company.6.

When I would go to our treated lumber supplier (Great Southern) to pick up a load, I routinely left with only half of what my PO stated because they were completely out of stock.

The guy wouldnt allow us to talk alone. the minute we moved a few feet away , he brought 2 bottles of water and came to stand next to us. we were getting really uncomfortable. he asked us to come back to the table/office so he can show us some docs.

The only way to take the "easy" rout in real estate is to take a passive investing approach, by putting your money into other peoples deals. 

So in a situation like yours, I would try to crunch the numbers and see where the line is in terms of what would put you in an uncomfortable situation vs best case scenario.

I haven't had such a bin in a long time (alley dumpsters), but I routinely forgot to put it out, even when it was full.

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

We routinely set our deposit amount above the rent amount intentionally, to encourage the resident to keep the place in good condition & to remind them that is separate from the rent. 

I would be especially uncomfortable if you plan to replicate that, since you'd be placing your road to wealth on an assumption.Now mind you, none of this even considers the other requirements to "convert this into a duplex."