I know it is not going to be easy but, why should I worry, i'm a bigger pockets member ;) Seriously, I had a few measure in place before even conceiving this endeavor. 

It may depend on what your expectations for an investment are but, conceivably, you'll get better appreciation in Journal Square, given that market prices there are generally still lower than JC Heights (although if you found a screaming and/or off-market deal in JC Heights, that changes the calculus).

Its access is via a ladder-like stairway (if that makes sense, kind of halfway between the two) and I wonder if the loft will create liability issues although there are very good handrails there is still an edge that someone could conceivably fall off of if they were being extremely careless.

So get advice on your options and approach a lender without pre-conceived ideas.

Conceivably, these siblings would either list and sell the asset to your investor (for which you receive commission #1) or you bring in a developer/syndicator.In the second scenario, siblings would partner up and contribute their equity into the formal or informal partnership and the developer/syndicator would bring experience (successful track record), and other resources including builders, design architects, engineers, and entitlement experts for zoning and building approval, depending in the scale of the project.A third choice exists whereby siblings attempt development themselves.

I've conceived of notions such as letting the taxes go delinquent and then buying doing the tax lein foreclosure process on it?

Renters will have to leave by this upcoming mid-summer.If this is allowed to stand, the units would be for a very different market for investors, negating not just long-term rental landlords (like my aspirations), but conceivably AirBNB-like models.   

That's what most of them say.....Fun fact about myself:I am 1 inch shorter than when my youngest daughter was conceived and then born....motorcycles are FUN and apparently dangerous, but I can't wait until I can send my two girls off to college and buy another bigger one....2 wheels are life!

But most that I've seen will not consider it unless the investor is bringing $500K + to the investment (your amount would conceivably make it worth their while).  

And the older you get, the harder it is to conceive and the higher the chances of birth defects (most people don't know it, but it's true for older men too!)