I'm aware of the dangers of doing business with friends, but I wouldn't rent this furnished house out to anyone else, and I'd rather not eat the $1900 mortgage. 

The roof may have 5-10 years left on it.The $30/month does eat into our monthly cashflow, but want to get the pros and cons of both.

I am currently making my way through Brandon Turner's property rental book and one of my questions is, during your analysis of the property and initial estimates- how do you account for property tax - or the potential for it to eat up your cashflow at some point?

As mentioned earlier, low rent properties have risk in that one major repair like a roof can eat up many months or rent.

Is the kitchen near the eating area?

I have entertained the idea of getting my real estate license (so we could be saving money on our buys and sells) as well as helping take care of the odds and ends errands that eats into my husband’s time (running to stores for materials, fixtures, etc.).

(My numbers were based on a $1M purchase of a  5-plex that rents out for $1500/mo before raising rents and the expenses eat up all the rental income.)

Take control of the deed and understand your Aquisition Costs, Closing Costs (Realtor Commission, which to be Frank, can eat up quite a bit of equity), Holding Costs, and in regards to seller costs...

For the broken window I would eat it. 

Take a look at below options and let me know which might be best. 1031 would keep 19.5k in additional deferred taxes to be used for new possible property, but easier said than done.option a: 1031 into another SFH property for 175-180 range with a mortgage and get mortgage for remaining amount. 20k mortgage seems like a waste.option b: eat the 20k tax and use a straight sale of property.