So I'm not sure how to gauge how much of a hole this issue could become.

When you find yourself in a hole, stop digging. 

The trucks broke all of the drainage pipes under the drive way, they are still able to allow water to flow but the edges of the pipes are sharp so if tire hit it the wrong way then it may put a hole in tire of a vehicle.

Tax liens can be purchased for as little as a few hundred dollars for very small properties.The problem is that each state and county have its own regulations: they issue sale lists of tax liens certificates throughout the year, and auction dates are also different.Also, some states hold auctions once a year, some twice a year, some every month..So, I went on a rabbit hole and compiled a list of the next auction dates:November: Colorado, Illinois, Louisiana, Montana, New Jersey, Ohio, Pennsylvania, Vermont, West VirginiaDecember: Illinois, Louisiana, Montana, New Jersey, Ohio, Pennsylvania, South Carolina, South Dakota, VermontJanuary: Arizona, Louisiana, Montana, New Jersey, Ohio, Pennsylvania, VermontI actually have the whole year mapped out with websites where you can get the sale lists.

Much cheaper to maintain and on the electric billand etc.I only build cabins in the woods though so again, the drainage would be the issue if you are more in a neighborhood or something. 

Allstate and State Farm in Illinois lately have been huge a**holes as far as providing coverage when a loss occurs.

Curious to know if anyone actually did go down this rabbit hole?

With no equity and negative cash flow from the get-go, I'd say if you want a hole to throw money into, get yourself a nice boat. 

If your properties are located in city with SB 721 enforcement mechanisms in place, I would contact the city for inspection guidelines and then find an inspector and contractor who understand those guidelines.At the risk of sounding undiplomatic, I have zero desire to pay someone $4K to drill holes in my balconies.

He will face an increasing amount of pain and pressure for many years before he digs himself out of THAT hole.