But, the more uncomfortable you're willing to be, the better the deal will be most likely. 

Basically, if you are committed to this investment thing, you will need to make some uncomfortable/hard choices to eliminate the credit card debt and lower your monthly debt.Once that goal is complete, you can begin practicing habits to live below your means and start building up your savings. 

This will at the very least make the future conversation and announcement of the increase less uncomfortable for everyone. 

If you're uncomfortable with documents, get a business lawyer to write them for you.

Not sure I would even invest that much, but might give you a start.My suggestion if you feel really uncomfortable learning on your own....go join your local REIA. 

I have quite some questions that need your help: For tenant screening, I plan to do the routine background (eviction, criminal) screening and credit check.

That seems odd since most RE niche tax strategists deal with both sides routinely

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

Her claim is that her disability requires that she not move furniture and further that she is uncomfortable with anyone else moving her furniture and her mental health disability requires this accommodation.

Do they want a custom front door different than all the others in the neighborhood, or will that make them feel uncomfortable, and so they want their door to be similar to everyone elses.Do you know how to spec high end finishes, and do you know how to inspect and approve high end finishes for cutting a check  to the contractor.Will you spec all seems caulked on all interior trim before painting; why, why not?