Here are a few I recommend: "Rich Dad, Poor Dad" by Roberto Kiyosaki; "Set for Life" by Scott Trench; "The Unofficial Guide to Real Estate Investing" by Spencer; "The BiggerPockets Ultimate Beginners Guide" found here on BP; "The Book on Rental Property Investing" by Brandon Tuner.

Even in the midwest which offer nice beginner markets where one can get in for under 100k on purchase, you will need 40k+ and the more the better. 

My wife does tell me about what I can say concerning the things I've learn and to be sure to not call it advice.

This would allow me to raise the rent for the main house a bit over market but I'm concerned usage could get out of control and making my cashflow take an unpredictable hit.Does anyone see other options here that may work better than the two above?

I'm concerned with how to enforce any rules now that he's trying to skirt the lease.

Inform your LTR tenants about these rules and let them know they can report any excessive disturbances directly to you.Communication: Keep an open line of communication with your long-term tenants, so they feel comfortable voicing any concerns early on.Outdoor Amenities: If there's a shared yard or patio, think about dividing these spaces further to give both STR guests and LTR tenants their own zones.Protecting Your STR from Bedbugs:Mattress Encasements: Invest in high-quality, bedbug-proof mattress and pillow encasements.

We kind of stumbled into it and keep stumbling as we go but not having a plan or framework for business is a major concern. 

Never talk about being an agent unless the question explicitly concerns that.

What I personally experienced was the under-capitalized beginners running out there talking multiple sellers into doing this..

@Rebecca Morris The Bigger Pockets bookstore has a great collection of books on multiple topics that are beneficial to beginners.