Asking the MF Group     What's your purpose here, is it to grow your:- Network- Knowledge - IncomeI understand ultimately that these seemingly unrelated dots ARE connected, but why are you here, this is a great opportunity to share your story.

I believe that any losses you have in the stock market could offset rental income.On the other hand, the better solution is to not have any net rental income. 

@Nicholas DillonI wouldn't pay off any of the houses.

I think LLCs are over rated unless you have to hold the property in one for financing like most DSCR lenders will require.

My gut says you probably want/need separate policies for the different entities at the very least - the purpose of having them is to keep things separate in case of a lawsuit, so combining insurance would pierce the veil and allow someone to come after everything. 

These are the keywords that stand out to me in your question:sources, websites, best deals, systems, step by step, factors.You are focused on all of the wrong things.

One tenant had a lease that has since expired but that lease wasn't triple net and the other tenant never had a lease because it is the family business but the lease is triple net.

The accuracy depends on the quality and recency of their data in your market.

Not at all-Just deliver what he took money for -Plans for an efficient functioning of the building.

Your peace of mind matters.You’re not late—you’re just starting fresh, and that’s powerful.