But if you have lived in the rental for 2 of the last 5 years, you should be clear up to $250k/individual or $500k/couple before you're hit with cap gains. 

It's important to do thorough research and lean on those who are more knowledgeable in the field.  2.Strong Stomach: Many individuals who jump into investing end up sinking before they can learn to swim.

That policy rides on top of your individual policy limits.As far as what company is the cheapest, nobody can answer that because no national carrier is the cheapest in every market.

Should I price each individual piece as a stand-alone investment and then combine them for a final offer price or are there either hidden challenges or advantages to a sale like this that would either make it harder or easier to manage?

In fact, I've heard numerous house hack stories of individuals doing exactly what you have mentioned.

What if one individual leaves and a new individual joins in their place (I've never had that happen)?

Joint venturing and partnering with successful individuals can be a powerful strategy.

When an individual property is distressed and hits the market, it's not going to have those instant 12 offers and bid wars flaring up over them that you will see with those purdy perfect white picket fence Hollywood dream homes in areas with optimal school districts for their kids, etc. 

This break-down all of the structure/land requirements you need for each individual zoning.

I'll re-post and ask the questions in individual posts.