I once had a financial planner tell me to sell our 2 apts and put all the proceeds into the stock market.

I've always been a planner, and I've always been good with money thanks to my parents (they gave me an allowance based off of how often I completed my chores, and had me use that money for buying clothes, shoes, or any extra things for myself).

I had a discussion over the phone with the city planner before buying the property and received lots of positive feedback in support of severing a lot and adding density to the downtown region.

He is an extremely knowledgeable financial planner, but he also holds his Colorado Real Estate License and understands/advises in real estate acquisition as part of your overall portfolio.

Can anyone recommend a financial planner who is familiar with RE investments?

A planner at the P&Z commission can tell you the process, its requirements (often around parking), and the likelihood of it being approved.

No problem with the permit processes, city planners, utilities.

Sounds like you should talk to a financial planner and/or an accountant.

My two cents as a former city planner....

Also if it is a planned development or HOA community you can also find out lots of information from the formal planners including civil engineers who helped plan the community who have further details including original documents that the county or town may not haveAlso, government offices such as DEHEC, US Army Corps and DNR are all valuable resources if you ever have any issues that relate to wetlands and they will conduct an investigation for free if it is required and you submit a request.