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. 

I like your post and you obviously know Chicago but a lot of what you are saying is just plain wrong.

BUT, I am sick living in construction and would like to move to a new home and then finish fliping and sell or hold the two homes asap.

As long as you have the insurance liability, property and flood if you are in a flood plain.

I'd make sure it would do well with long term in case you get sick of mid term and want to convert it to long term.    

BUT, I am sick living in construction and would like to move to a new home and then finish fliping and sell or hold the two homes asap.

I got my GC license a couple years ago so I could build houses myself as I was sick of dealing with contractors.I've hired plenty of contractors that were not licensed/insured and it went fine.

Insurance protects your property from paying out of pocket for damage, plain and simple.

Perfect for today’s market.Speed of Approval: He was aproved and had access to funds within two weeks, which gave him the edge to close on a high-potential property.Clear Communication: The team explained everything in plain English.

If they’re violating the management agreement, state your case plainly and try to work it out.