I'm looking for someone is willing to spend time with me and maybe teach/talk/travel around the city some.

If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

When I talked to a rep they said I could not be refunded that amount and now my trial has expired, so in order to spend my $48.61 I would need to spend $59 for the month. 

Spending on expensive upgrades is not the answer to improve your tenant base in this type of area.Keep the homes habitable, clean, and safe. 

Frankly I would be less excited at spending any kind of money on a place that I don't own.

How would you recommend, or what resources would you refer for us to properly figure out how we spend our time and appropriately get compensated for it?

Like @Jesse Rivera mentioned above, I also go to a few sessions but spend most of my time in the lobby or at the bar making connections."

We discuss spending, net worth, and future investing goals with the cash.

Also, what if you spend thousands of dollars on a brand-new DADU, only to have the seller reaqcuire the house?

To the nuts and bolt question of what defines occupancy, it is the place you reside and spend the majority of your time/nights.