This wasn’t an issue for us for this home because it will be kept in the family for years and hopefully generations to come - so we thought why not depreciate now! 

Things like power outages during winter storms, septic clogs due to misplaced products into the toilet have been the biggest issue.

I had them sign a lease addendum for communication and charges.

Here are some considerations:Rent-by-the-Room Strategy: Market Demand, Legal Considerations, Property Configuration, Lease Agreements, Screening TenantsManaging Remotely: Automated Systems, Local Contacts, Virtual Tours, and TechnologyProperty management companies: communication, client reviews, services provided, and local expertiseTo make sure local laws are followed and to discuss any possible legal issues, speak with legal and real estate experts before moving further.

I have communicated with my buyers, some are are not interested in new construction idea which is odd lol, maybe im not explaining correctly or to much risk ?

Everyone's house has an issue if you look close enough. 

He is terrible at communication, so it's hard for us to even have a conversation with him to figure out how we can work with him.I already have a lawyer in mind to use for eviction services, but I would like to avoid getting to that point if possible.

Consultants, inspectors, and mentorsProperty managersAssistantsBookkeepers, accountants, and attorneysLandlords if you rent your office spaceYour business partners if you paid them (except if they were strictly lenders)Disclaimer about wholesalers: it is a controversial issue, with some of my colleagues claiming that wholesalers do not need 1099s.

I need to look at the numbers again and make sure this is a risk I am willing to take on but I imagine there are better flip opportunities that yield similar returns and may carry less risk as I am aware finishing a basement can yield all kinds of unforeseen issues.

Property taxes different issue- depends on state and city and how many months arrears.