The market has definitely gotten more competitive, and it’s common to see BRRRR deals over $250K, especially given the high demand/appreciation in the area.

2-4 units are not that common, but builders are building them more now.

You asked about buying older properties and the biggest issues I have found is that roofs need to be replaced, HVAC needs servicing/replaced, and sometimes there are foundational issues (not super common). 

Commonly known as xxxx.

@Natali Cobb depends on what is common for the area.Also, you can put in your ad that W/D negotiable and see what the responses are.

You will likely have common area lighting (interior and exterior), perhaps heating and cooling too. 

In your experience do you see people commonly attempting to offset ordinary income / W2 with syndicated losses, despite the above?

It's common for traveling medical professionals to extend their contracts.

"Is it a common practice to report it as a loss even though I fixed it out of my own pocket?" 

Both common area TI and unit specific TI.