I have been completely plagued by analysis paralysis and am finally attempting to put an actual deal together! 

Correct me if I am wrong, I can't see any other reason you would be charged this.In my opinion this PM is being completely reasonable.

Your father is not completely wrong.

A representative of the state came back saying the sellers owed $27,000 and it needed to get paid before a sale could be completed. 

Hell, maybe one day Saudi oil will be a currency reserve, a complete reversal of oil being traded in dollars. 

If I use my own cash, it would take a long time, perhaps 4-8 months to complete the work.

It's on the location you bought, but it's completely different property with its' own ownership records.

Mickey just completed roofing, siding, windows, soffit and fascia on a property for me and did an excellent job at a great price.

We pre-purchased a new construction home in October 2017, and it's scheduled to be completed by April 2018.

The buyer doesn't perform you typically have to just go file an eviction just like with a tenant except when is the bond for deed filing eviction it will usually take about 45 days to complete the eviction process.I've done a few over my time both buying and selling and it's not that difficult.