Maybe land isn't the way to go? 

Looking more closely the higher price agent seemed to provide overall better comps though one or two that I would have considered comps at a somewhat lower price didn’t make it.the Lower price agent had a very unimpressive CMA which included a hurricane damage property sold for land value and another that was an auction, so in retrospect, I’m not too convinced that the lower price agent really knows what they are doing. 

Unfortunately the photo did come through with Ja and Desmond...i'm sure that was a fun experience.Have you heard of the REDI program sponsored by ULI, the Urban Land Institute?

In sum, I need the land for my DADU, and the Seller needs $200k cash.

Reach out to my survey and engineering company that is doing our plans for our land.

Let's assume that the neighborhood is a C class and the median income of the city is greater than 3X of the market rent.Here are some of the considerations I've come up with so far:- Units are in need of renovation and capex is too high or not available- Unit quality is not the same as market - Seller is worried about losing tenants due to increase- Vacancy rates are high or filling units have been difficult- Rent increase would take multiple increases over multiple lease periods to get to market rate if seller is trying to retain the same tenant- Seller inherited property and just want to liquidate- Seller needs to liquidate quickly (financial burden, sickness, quick exit from land-lording)It seems like I might be missing a warning sign about a deal if they are selling with current rents that are under market; but again, this seems to be most of the properties I've underwritten.And in the same vein, what should I be worried about when purchasing a deal with under market rent with the intention of raising them after purchase. 

Should I play harder and get into land development?  

Chris, I work full time remote and specialize in land.

Being fairly new to land lording I felt the need to gather a bit more insight from other seasoned professional with how to proceed, but you're absolutely right. 

Land is valuable as I could purchase a new mobile home and install and less costs since utilities are already on the land.