-asphalt parking/driving(currently dirt with massive pot holes)(awaiting estimate form local company)-Individual metering (previous hotel, 3 different buildings(2 doors, 7 doors, and 6 doors), all on one meter)Any advice or things to consider are appreciated.

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. 

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.

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. 

You need to pull a permit, then the Contractor has to take down the coping and bond beam a couple feet, then core holes in the pool floor (so it wont ever popout of the ground).