New in Chicago - non-pro landlord and agent

[Kirstin Rogers]

Hi all. New here. I am interested in figuring out what to do with the property I have and how to best allocate some funds as investments. I am an agent and a live-on-site landlord in a three-flat in the ever ridiculously appreciating West Town. I work downtown and would like to have someone help me analyze my current property and help figure out what should be done (maintenance/updates); what can be done (1860s foundation); and what makes sense to do (to keep up the rents vs the prospect it will be torn down if I sell). I would also like ideas on how to invest in other properties while having capital and a day job, and not being handy. I am a licensed agent but I work for a bank and their policy will allow me only to conduct deals for myself or family, so currently my license is with NIREIN. While I have other investments, that same policy limits what I can do with securities, so real estate, as long as not REO'd by my bank, is fair game. I want to keep living in West Town and prefer direct ownership vs condo situations but my budget means it is highly unlikely I would find another freehold in the area. Have considered 1031 exchange but that would work only if I found a local 3-unit that is larger than mine. I know the taxes will kill me if I don't do that. Cheers all!