The disposition of SFH's in markets that fail to turn is one of the most overlooked and grueling aspects of this strategy.   10 Years ago when I first began investing I grew a 30+ SFH portfolio in a neighborhood in Northwest Philadelphia and it pains me to say I fell into category 2.

Try to look for deals, play the long game, but if the number's don't add up don't feel compelled to do anything now because you'll just feel maximum pain a year out after purchasing. 

I own 108 acres of land in Carlisle South Carolina that I would like to sell. Part of the property (1/4) was owned by a relative, *I own the rest) that died ten years ago in Pennsylvania. The executor did not properly...

Craigslist or Facebook marketplace did came to our mind at first but we are afraid to find someone who would randomly stop paying rent and become a pain to evict. 

Sure, they play pot odds and ensure they only take on good cases.So... it depends on your W-2 hours spent... and your tolerance for pain (risk).

Personally I see money orders as a pain to deal with both for the tenant and for myself by adding unnecessary steps. 

Totally agree that giving it away to taxes was a very painful experience for me!

Instead of spreading the "pain" on all, you look to different factors so can effect a smaller universal price increase, and start being more focused on the other price increases to be a burden upon those specific customers that it applies to, better known as a fee schedule. 

Unless you already have buy & hold investors lined up make sure you have a reasonable inspection period as showing occupied properties can be a real pain unless your buyers only care about the rent & purchase price.

Gas grills are a pain to properly clean.I didn't notice that much of Disney themes?