Major structural issues and unforeseen liens are the two issues I fear the most.(1) How do you seasoned investors go through the due diligence process when you’re vetting a property prior to auction?

Depends on your facts, circumstances, and goals.If you still have questions I'd encourage you to have a conversation with your accountant post 10/15.Best of luck.

Under normal circumstances a first time flipper often does not do very well.

Under what circumstances would you ask to connect?

If you are looking at any multi-family of 5+ units then that would be commercial loan or hard money.Conventional has a couple programs (one with Fannie Mae and one with Freddie Mac) that can do as little as 3% down depending on the circumstances and they also have a 5% down.

My life circumstances have changed and I’m looking to decrease my monthly expenses and reduce the time required to maintain my 19000 sq ft yard.I’m waiting to see what happens with the comp plan zoning in 2018-19 and hoping the market doesn’t tank.. but it n the mean time.I’m looking to infill the lot.

Education is the single greatest way to up your economic circumstances, I wouldn’t simply dismiss that.

They can also ask the inspectors superior what the expectation is for this circumstance, being that the plans are already permitted for the site.

IRC 469 deals with passive activity loss rules and doesn't relate to the 'trade or business' question at hand here.Although your individual facts and circumstances must be considered, there's volumes of case law that show the tax court generally (but not absolutely) regards even a single piece of rental real estate as a trade or business.  

And it would have to be extraordinary circumstances for me to pay for a repair person at this point, it so often is a waste of time and money.