Your happy the machine is finally running again but are surprised when the insurance company tells you they are only covering 1/3 of the expenses, because things like freon, freon disposal, and a host of other services are not covered under your insurance policy. 

Be safer to get a regular investment mortgage than to commit fraud.

Also what specific expenses are needed to calculate regular upkeep for property? 

Unfortunately, the DC, Maryland Virginia area doesn't host many properties in this price range that are easy to grab hold of.

Once the realtor rents the place, then you should just be on regular management of the property. 

But one thing it does seem would be beneficial would be to use an accountant that's familiar with every possible way to deduct your expenses now- someone who invests themselves or works with investors regularly- there may be things that qualify for expenses vs capital improvements that weren't accounted for. 

I'd figure my regular job paying what it does would allow me to cash out no problem.

@Michael Baum Yes, you are correct that regular preventative maintenance is key, as well as having a good local handyman.

Minimal duties include: obtaining monthly dues, tracking delinquencies, thorough bookkeeping, regular communications to owners of budget, hosting a website, regular maintenance on the property, and managing and vetting contractors, managing contracts and renewals, etc.

Going one step further, a host could have a member of my team dispatched to the property if they do not comply with requests to shut things down.