My ideal living is not close-quarters apt. complex, even with amenities I couldn't afford on my own like pools, gyms and social areas.

Demand for living quarters is universal.

Unless you are making $100 an hour, painting yourself might make sense.More than three-quarters of the calls you will get when listing on your own are realtors slightly discouraging you in hopes that you give them your listing.

So if you decided to sell one or more of the properties down the road, you could do so through another 1031 and continue to defer taxation.

The agreement can be whatever you want, just like an online advice :) However, for taxation purposes, this idea of @Carl Fischer will not work without modification.

The house is on 1, a 2nd house (servants quarters) is on a second lot with frontage, and the other two are land.

One way or another you are going to pay for your "tuition" - either a. being scammed by gurus hoping they will teach you the "secrets" on how to become a millionaire in your first year/month/property/flip/deal, or b. while doing mistakes in your first projects/deals (but at least you get something out of it and is the best form of education)  or c. putting a lot of time, effort and resources in learning about real estate investing industry (and that includes marketing, financing, negotiation, contracting/legal, taxation, hiring, project/people/property management, etc.).

Aside from the student loans (a separate little loan from every quarter or semester) I used the snowball method like Dave Ramsey teaches.

Tenant agrees to keep quarters clean and in a sanitary condition.

My exterminator now does quarterly sprays and knows to keep an eye out and I will charge back tenants if they come back.