After that year and a half we looked into buying but another family member my grandmother asked me if I was interested in moving into her rental that she has had for ~40 years in exchange for putting in labor to fix it up for sale.

I think it does but just want to see if I am correct on this, as if this is correct I can potentially pay very little capital gain tax on it at the end, thus saving myself from having to do a 1031 exchange. 

You could have done a 1031 exchange to defer capital gains taxes, however, it may be too late for that now as there is a time frame for which you need to identify the next investment property and close. 

In exchange, I would like "X" number of CMAs per lead and $100 cash."

It's the promise that when you want to exchange your "promise to pay" that there will be money/gold to cover your call.

Please let me know your thoughts. if your exchanging renting with owning and your exchanging 1900 dollar rent for 500. 

For example...Real estate is a tax-advantaged investment in several facets (depreciation, capital gains, 1031 exchanges, opportunity zones, the list goes on and on).

Rather than being a solo dealmaker, I want to build upon my meaningful relationships in the area by getting to know motivated wholesalers, investors, community banks, and other professionals who enjoy exchanging ideas and knowledge.Does anyone have any advice on meetups for local investors, good wholesalers, small local banks with less rigid financing, or ways to find other cool people that love what they do?

Even though both properties are being run sub-optimally, they have appreciated in value where I'm considering doing 1031 exchange for both. 

My question is can I still do the 1031 exchange?