All Forum Posts by: Jonathan Klemm

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Hey there @Danny Santana - Wow!  Sorry to hear about the squatters.  How did you end up getting them out?

Sounds like you have some good cash flow, and Pilsen is 100% a great up-and-coming Chicago neighborhood where you will have solid appreciation over time.  I'd suggest keeping it!

Where is your parents house and why is that even an option to turn in to a multi-family?  Do you already own it?

This is great information @Daniel Bourdeau!  Appreciate you sharing!

I'd be curious what the HOA dues are for these places because I know some of the Chicago condo fees are nuts and can completely blow up an investment/AirBnB deal!

If any Chicago investors are looking for short term rentals I am sure they'll look to you, since you are providing great info and have fantastic experience in the market!

We need some more information @Keenan Cromshaw...

What exactly are you trying to do?

You should hire a handyman for stuff that requires a handyman (i.e, fixing locks, painting, minor plumbing work) and hire a general contractor for larger renovations that would require permits/licences/etc.

Sounds like you know the answer...use both based on the particular situation.

I'm in Chicago and use both on a regular basis.

Hey There @Maya Jones!    I usually give my tenants a text because my Chicago buildings are only 2 units and they hear me and I don't want to surprise or scare them!

Tenants should definitely not use common areas to store stuff or use the common area electrical.

Document everything via email about notices, and just do everything politely and with respect.

@Jason Marcordes do you guys handle this in any special way?

Hey there @Maya Jones - Could you explain what the binder method is?  I'm also not familar with it.

Either way, I would give them notice ASAP and EXPLAIN WHY. If you are making a significant jump, provide some details of current rental comps that they understand, why the increase is so steep.

Chicago is tricky, so definitely make sure you follow the notice requirements.

Just curious, what is your current communication and relationship with the tenants like?

What's going on @Zachary Overstreet from Aurora!  I'm from Aurora's sister city, Elgin, on the NW side of Chicago, but live and work primarily in the city.

Highly recommend checking out some of the local meetups throughout the chicagoland area.  Here are some that are posted on BP:  https://www.biggerpockets.com/forums/521

I'd just remove the word "hopefully" from your post and commit to house hack in 2026 ;-)  Happy to help and guide you any way we can.

Are you doing any investing in Chicago @Charles Clark or are you primarily investing close to home in Milwaukee?

We really like the format of Cashflow vs. other meetups...it tends to be more engaging rather than just listening to a speaker (which is of course great as well)...its just a different vibe.

Hey @Eric Flatt - You got a ton of great feedback above from several other Chicago investors.

Did anything change with your search?

What's your max purchase price and desired cashflow per door?

Hey @James Wolf - Great areas of Chicago!

Do you have any more details on the seller financing terms?  How many buildings in total?  Are they wanting to sell as one package or willing to break it up?