In my experience, most of the "wholesalers" I run across send a few postcards, hang some plastic trash on telephone poles that neighbors have to clean up eventually, and offer way too much money on a property then call you up and say they've got a "deal" for you.

You can also offer that they only have to take what they want and can leave whatever they don't want behind (that saves them on cleanup and moving costs).  

The HOAs tend to eat up your profits and give some amenities to the tenants...like pools and fitness centers, gated parking, yard care, neighborhood cleanup,  etc, that I don't think they are often really willing to pay for or better yet, pay extra. 

His friends were supposed to clean up and paint the wall, put the blinds back, etc.  

Liability.Why go through the hassles, repair costs, and clean up?

Had I not bought in cash I would be in a negative cash flow position after a tenant turnover which required more maintenance and repair/cleanup than anticipated.

The clean up costs were 2/3rds of the budget for the entire job . ( I felt sorry for the guy )  The addition was never built .The one thing you forgot , a good contractor will properly vett a customer and also ask for a drivers licence , check to make sure he is the legal owner of the property , check for judgements and liens , and how many lawsuits the customer has been involved in . 

When people ask us, we tell them that allow well-behaved dogs for a $25 pet fee and state that they respect he following house rules:Tenant needs to clean up after it in the yard No animals on the furnitureNo Wet/Muddy Dogs in the houseThen we provide a little doggy basket with a towel + lint roller.

I am looking to hire someone to do bi-weekly cleanup, grass cutting, basic yard maintenance on a property in Boston/Dorchester MA. 

Also look into lenders who allow asset depletion to qualify.