And my #1 issue is I don't see any actions to address this in a meaningful, market specific manner. 

Quote from @Christian Styles: Potentially able to help you find someone but I would need to know specifically where the property is in order to know who to recommend.  

However, you could look into a “construction exchange” where the funds are used to improve a new property acquired through the exchange, but it must meet specific IRS rules within the time frame. 

- Usually a 5 unit with a boiler means that all the units share the boiler heating system.Which specific utilities in which units are paid by tenants vs shared?

If they’re late a third time, you have a strong case for eviction for habitual non-payment—without risking the tenant showing up at the 11th hour with the money.For your specific circumstances, with only a partial month behind, I would guess there is a decent chance they can come even on rent and it would be a waste of your time.

On the specifics of this 700 a month program.. its small money and if you get inspiration from it then by all means.. but so many ( not saying you of course) will go into credit card debt for this stuff.. that's no beuno .. 

From the public website,The BetterLife Tribe program offers everything you need to achieve real estate success:Monthly Calls with Brandon Turner and top real estate experts, providing you with insider knowledge and strategies.1-on-1 Personalized Coaching to tailor a growth plan specific to your goals and challenges.Access to the reiOS System of Success, the exact operating system Brandon used to scale Open Door Capital to over $1B in assets.World-Class Real Estate Education and Tools that equip you with the skills to dominate any market.A Thriving Network of 1,000+ Active Investors ready to support, inspire, and challenge you on your journey.Seems like a great program like many do in the marketing materials

What specifically are you wanting to learn?

Consult you insurance broker for specifics but I found this policy to be very protective and reasonably priced.With regards to an umbrella policy they are typically good to have.  

You will want to consult with a lawyer.In regards to your last two questions here's some background on what makes a contract valid and enforceable:Offer: A promise to do or not do something within a certain time period Acceptance: A clear and direct statement that all terms and responsibilities are accepted Consideration: A legal and adequate inducement given in exchange for the promise Capacity: The parties to the contract must have the legal capacity and competency to contract Awareness: A party must be aware of the contract Legality: The contract must be legal in the jurisdiction it will be operating in***Not legal advice*** Steps I would take: -Review contract in detail to understand each counterparties responsibilities (if you are not aware)- Email a copy of the lease to each of the tenants listed on the lease and reiterate lease expectations for termination notice, rent payment etc. - If the lease was signed via Docusign (other esign may have same ability) - you can go to the envelope, go to history and view the IP addresses for each action taken.