Once that's done, do I still need the houses to have landlord insurance or is there other coverage i need?

@Marvin Santiago 2 options, depending on how the property is titled.1)  If the property is in your personal name, your least expensive/best coverage option would be to write a Homeowners policy on the property you will occupy, with the 2nd building as a rental. 

People have abused the relatively flexible partnership allocation of the partnership items in order to shift income or loss from one partner to another in order to save taxes.Thus, IRS has a framework that can reallocate the partnership items based on the “ partner's interest in the partnership” if IRS determines the method of sharing the partnership items lacks the “Substantial Economic effect” (SEE)To meet the SEE, there are strict rules to maintain meaningful capital accounts including Deficit Makeup Requirement for those accounts.With the requirement, the partner must at some point contribute sufficient capital to eliminate the deficit, and, that way, the partner has the burden of the loss that partnership has and the allocation of the partnership will be respected by the IRS because there is SEE.This is a very high-level summary of the rules and is not comprehensive. there are many exceptions as well. 

Full benefits, comprehensive retirement planning, and some holdings of their own.

@Evan Parker you can go to the cities comprehensive plan to find out.

If it's not in a flood zone, a separate flood insurance policy is not required, however, you want to read your policy carefully to understand your flood coverage.

Where do you get your medical coverage if not covered by a significant other?

Where do you get your medical coverage if not covered by a significant other?

It seems like the driving factor for the cost is how much building coverage one gets so how much should I get?

There is simply no way to show a debt coverage ratio to the bank.