I know feedback on condos is mixed and I'm giving up some of the cashflow in return, but I'm concerned about remotely managing the bigger ticket items and this was my way of minimizing the risk.My question -- Are any folks familiar with renting in Middletown New York or know how to manage sourcing tenants has been for them? 

This would typically still cover any damages to the house itself, and any liability for owning the property, but would no longer cover the contents of the house, which is a fairly large line item within your owner-occupant coverage. 

Best you speak with several licensed electricians to get inspection/quotes.Just an item:  to convert a 110  system to 220 (at the box) a ballpark price would be $2,500+/- with all permits and inspections.  

I would also add that perhaps there's more improvements that were made throughout the year that OP maybe isn't considering (even like little items).in addition, items at closing (both at purchase at sale) also affect your basis in the property/gain on sale 

That is by far and above the #1 item at play here. 

Paint, maybe some new light fixtures, some low item updating etc. 

I'd say definitely factoring in the depreciation, age, as well as if they actually made effort to have it professionally cleaned.When back charging things from their security deposit, you have to provide the tenants an itemized list of what the charges are for...

What are the consequences of failing to disclose items such as unpermitted additions in a property disclosure agreement after a flip?

You should have a minimum of 5-10 ranked items on this list.

Document the items to be repaired and the cost and deduct from the security deposit.