@James Hong I'm all for the "If your offer doesn't make you a bit uncomfortable, you've offered too much" approach; however, as mentioned above, be able to justify it.

Routinely go to the property to check it out.

I typically check 3x a year at minimum, but due to family health issues and work, it wasn't possible to keep to my routine.

I would ask your insurance agent your insurance question, it may be worthwhile for her to get a renters insurance policy, it is not very expensive.If there is no written agreement you effective have an oral agreement, which in most states operates as a month-to-month agreement with all the normal laws and rules.We like to talk to tenants about uncomfortable situations in the beginning, when everyone still likes each other.  

Cheers to getting uncomfortable to get comfortable!

The next DIY aspect is the routine maintenance, such as yard work, leaf raking, etc.  

What do most landlords of single-family homes do for routine maintenance and service? 

So I will start you off with a story from 'da Bronx.I was in the basement of a 6 story old law tenament during a routine run and came upon what looked to be a secondary means of egress that was all boarded up.

@Jade Graue If you are uncomfortable with increasing your price to beat out other investors maybe adjust how your offers are written.

I was uncomfortable using the wholesale contracts found in BP's FilePlace.