They will smell the weakness and take full advantage of the situation.

This compounds weakness in the personal financial position.You've done a great job in repairing your credit, but I wonder if the other planks of a strong financial foundation, including a strong emergency reserve, and a strong monthly positive cash flow are in place.

We wish we could have gotten them out in 2016, but the local market was weak.  

I'd be inclined to non-renew a tenant who is chronically late and has returned checks however, regardless of the math.

If this is a single building space maybe they want to sell off for redevelopment in a few years or figure if the area is growing they can eventually dump out this tenant for a national one that could improve the value of the property.I do not know the asset class or who your tenant is you are representing.If they are a weak tenant I have even seen little to no leasing commission paid upfront and the rest as the tenant makes ongoing payments then the leasing broker gets paid also.The tenant reps say that the landlord decides whether to take the tenant or not so just pay the commission.

Please let me know if I am way off on the below steps, my LLC/title experience is pretty weak.

Good tools to use to learn about market rents include Rentometer, Zillow Rent Zestimate, and Zumper.The number of rental home listings and vacancies in the area also indicate how strong or weak the demand for rental property is, because high vacancy rates may lead to lower rents and poorer investment returns.3.

A property could appreciate in value significantly but if there currency gets weak against the dollar you could still lose $.

Matt, my current YTD ROI on the 401k is 5.9%...which is weak.

Not only is it a good way to identify goals, but I also think of it as an inexpensive way to spot weaknesses in my plan, identify false assumptions, and develop contingencies for the unexpected.