We see the quality of applicants and quantity drop this time of year historically

In other markets, it is possible to stabilize/make self-sufficient multi-family but it will be much harder in markets like yours.

Here's why: the rent simply isn't sufficient to cover opex and capex over time even in a best-case scenario. 5% maintenance is only $90/month. 10% cap-ex is only $180/month or $2,160/yr. 

It was a acting like a canal and the canal was sufficient to handle anything draining from that far up the sewer line.  

But I was taught to buy sufficient term life and call it a day.

First, basic accessibility is not sufficient on its own to exceed unit numbers in RT-3.5 zoning and an ADU is still subject to density restrictions unless your city has its own ADU ordinance or pilot program in effect on your lot.

You should also assess your holding and resale costs to ensure you have sufficient cushion to successfully complete the deal.Lastly, you should review all recent and relevant comparables (both before and after renovations).

Incurring debt before you have sufficient earnings to support that debt.

Consider focusing on quality over quantity, and on real estate with strong fundamentals that can do some of the heavy lifting for you.

Plus it could be an excuse to visit if (assuming it's family you like seeing occasionally - haha)$50K should be sufficient to work with in that area.