So, if a developer comes along and buys the mobile home park you will lose your entire investment.

Do you plan to further develop the agent side and turn that into a full time thing?

BTW, your "criteria" are likely just "rules of thumb" you developed (which is great!)

Ideally it pays itself back over the next few years and could be great!

If the number are close[100k or less], do preemptive due diligence [water, sewer, stormwater, planning and zoning] if the property is considered for a new build development situation.

I invest out of state in Pittsburgh from DC and self-manage everything, but it's taken me years to establish the right contacts, develop seamless processes etc. that allow me to handle everything remotely with confidence.

I want to get both tenants under triple net leases for 5 years ideally. 

Your development deal will look much like a flip in the eyes of the IRS since it is 6-9 months as well you'll have the short-term side of taxes, not the capital gains taxing on it.  

There are definitely some municipalities that are easier to get along with than others, but all are open to development.

If you had not team in those areas and could not have reasonably developed one, then you missed thing.You say you’ve done well in Chicago.