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).

I am a mediator in MA small claims court, have seen a number of landlord tenant issues where people routinely use attorneys and magistrates allow for fee recovery.

It is rough on the social life, but we have a nice routine of breakfast Sunday mornings before church at 8.

Routine items, like two weeks or a month of lost rent and $1000 in "make ready" between tenants are SOMETHING YOU MUST EXPECT!

I suggest routine pest maintenance.

But I’ve really struggled the past 5 weeks with a sense of direction, lack of routine, loss of focus etc. 

Commercial property management companies do it well but with commercial there is less "tenant and toilet" issues and more arrangement of just exterior routine maintenance. 

My cash flow numbers only include mortgage, insurance, taxes, routine repairs, and vacancies as expenses (I will manage and maintain the property myself).

What is your maintenance routine for keeping your rental property in good shape (roof, HVAC, etc).

An HDHP with an HSA has a handful of great benefits:  you still get healthcare, 'though with the high deductible you may pay a bit more initially for a year's worth of routine work out of pocket.