Rufo, so you are violating the HOA rules so I don't think they would cover anything if it is the fault of your guests.This will eventually catch up with you and could result in some big fines so maybe think of selling this or converting to a LTR instead.

My idea to achieve this is to convert the studio into a short-term rental.I’m trying to determine if I’m forcing this deal to work by relying on the short-term rental strategy or if it’s a reasonable approach given the numbers.

Currently our favorite idea is a SFH we can convert to an up down duplex by sealing off a staircase with an ADU on the property for us to live in.

Any investor or developer buy raw land lot (zoning code G) and go through the process with the city to convert to commercial use?

Converting a traditional IRA to a Roth triggers taxes on the converted amount, so plan accordingly.

.- The commitment letter says if I convert the leads given by the TL I would get a 50-50 split and if it was my lead through my COI/SOI while I was on the team, then it is a 80-20 split. - I had a few COI/SOI leads while being on this team who have not signed any papers with me or any one on the team as of yet and won't for the next 2-3 months.

But that's still a far cry from converting an R1 to R2 .

- Value add - How much does it cost to convert Non-climate controlled units to climate controlled units? 

You can always sale on your date and convert appreciation to monthly cashflow.  

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.