At least plan B does not sound a complete bad idea now.Thank you!

If you partnered with someone other than your spouse then yes, LLC was a good idea, since you now have a partnership.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

I have his phone number but wanted to come up with a good proposal before I call him and pitch my idea.

Any ideas appreciated? 

The only time I'd say it's an okay idea is if either: The area you're investing in is expecting so much appreciation that you will easily profit off that (watch out for mortgage interest though...the appreciation needs to be higher than what you pay in that and expenses to make it profitable)You have some specific reason for wanting to do it- family ties, future home, major long-term hold, etc.Maybe I'm forgetting another one, but those two are all I have for now...

I have several opportunities to snag up a self storage complex and a 18 unit apartment complex on creative financing .

Money isn't easy to save and $10,000( my debts) is a ton of money I want to save for a downpayment, I'm just starting so I don't have any money I would like to save $60,000 to buy a rental property, I think I could do...

Then I started to contact brokers that bought and sold Apartments complexes and proceeded to 1031 exchange all my Condos for Apartment complexes and told my story on BP Podcast 238 in 2017.  

Does anyone know, or have a good idea, about the difference in returns on entitling & developing the land for each scenario, with final objective to sell to a builder to build and sell the structures him/herself.