Like aircraft checklists and vehicle operators manuals (the -10s), one can benefit from extensive research, trial and error, and deliberate improvement principles gained by the many that have gone the path before. 

It sounds like you have a solid system with clear communication on extensions and vacancy openings.

Usually when wholesalers can't find a buyer before the close, they will try and get an extension.

I don’t tend to do much plumbing drawings, especially when it get complex or extensive. 

This process is extensive, requiring community engagement and approval from the City Planning Commission and City Council.Given the predominance of multifamily residential properties in your area, there may be a precedent for such developments.

If I wanted to get more involved and spend more time on investing (like if I was 20 years or more younger) I would make extensive use of options.

However, if you have a more extensive portfolio or plan to become larger in the next year or two, I would look for a double-entry system that allows bank reconciliations.

Optimally, the lawyer or the firm should be familiar with public infrastructure that developers are typically asked to pay for, such as road widening, turning lanes, new roads, sanitary sewer extensions, new water and electric extensions, fire hydrants, etc.

However, I am curious to know your reasoning behind considering bidding on a property that requires extensive rehabilitation, including demolition.

The three ways to handle the risk are (1) gaining knowledge and experience in both investment in general and in the area you’re investing in specifically (2) extensive due diligence and when the inevitable bad outcomes occur despite (1) and (2) then (3) diversification.