They either:- Completely dump everything on us and then aren't happy with the results, or- Try to micromanage us, which we can't do as we aren't paid enough to be "personal assistants". 

As a result, I stand to lose not only my due diligence fee but also the escrow money.The situation has become even more concerning.

Reporting these expenses on your personal tax return (likely Schedule C for a sole proprietor) could result in a net loss that might offset other taxable income, reducing your overall tax liability.

I recall reading something in The Economist pointing out how these not-so-obvious markets often bring steadiness that flashier spots can’t always match.

The net result is basically the same, but it keeps the two properties separate from a lenders perspective.Any low down payment money, particularly on an investment property, is going to come from a private money lender.  

I've done this a few times and it usually results in a monetary payout or the seller kills the next buyers deal. 

Can you mix and match tenants to fill a larger space?

I tend to do a quick dirty look at a building like JW with price per door, but after that sniff test, I quickly like to understand $Cost/SF and $rent/SF.The way I look at a single family, 2-4 units, or a 20 unit is all different, but the end result is still ROI or IRR (over time). 

Fourth: even if the entire deduction is available, it results in much smaller automobile deductions in future years and extra taxable income when you sell the vehicle or trade it in.

The result is an even deeper inflation than what we already suffer from.