Rolling money into a new deal through a 1031

[Abigail Gibson]

Hey all - first time poster, long time listener. 

I would like to expand my portfolio but I have a hesitant partner so I am working on doing this slowly. I own a rental home, a personal residence that I turned into a rental, with a 2.75% APR 15 year mortgage.

My current cash flow is around $375, but once the house is paid off, in about 7 years, I will cash flow around $1200. 

I put $100,000 down on the house and did approximately $10,000 in repairs going into it. 

My question is, should I sell the house and roll $135,000 into a four-plex that cash flows around $800 a month? I would be putting myself into a 30 year mortgage, rather than a 15 year, so I would achieve the higher cashflow number at a much slower rate. I have suspicions that the rent is undervalued in the 4-plex, but where they currently stand my cash-on-cash numbers are between 6%-8% return depending on if I have to put 20 or 25% down. If I did this, I guess I could take the remaining $65,000 I am going to get from the sale of the house to purchase a second rental that could also cash flow. 

As I have started running numbers, I have found that I am stuck in the classic analysis paralysis more than I thought...