Cash strapped: How to Finance a pricey 3-flat?

[Heather Shannon]

Hi All!

I'm so happy to have found this community recently-what an awesome resource!

I currently own 2 condos in Chicago: 1 in Uptown that I've had a year-long renter in.  Her lease ends at the end of the month and I plan on selling it in June because the association won't let me do AirBnB and I find that to be a much better use of my investment dollars than regular renters!

The other unit I own is on the East side of Wicker Park and is already working well for me as an AirBnB.

I plan to take the money from the Uptown sale into a 1031 exchange to then invest in a multiunit property that I can do AirBnB with. The properties I'm interested in are 2 or 3-flats listed around $900K. The problem I'm running into is the FHA loan limits and the high downpayment required for conventional options (which are still limiting in their maximums).

Based on the area one of them is in, it would qualify for the HomeReady program which requires only 3% down, but I don't know if HomeReady will work with Jumbo loans or if there's a way to do a 1st and 2nd loan in that scenario that would still leave my downpayment low (around $45K).  The City of Chicago I think has a downpayment assistance program starting soon for up to 7% of the purchase price and it includes multi-unit properties (and you don't have to be a first time buyer), but I'm doubting they're really going to gift me $63K . . . 

So, if anyone has ideas on financing this type of purchase, I'm all ears.  I'm newish to real estate investing and have never done a jumbo loan or purchased a multi-unit property!

Thanks,

Heather