I did the house hack route, about to buy my 3rd now. 

Looking at buying an investment property in Jacksonville, Florida from JWB Real Estate Capital.

The exception would be if this was already permitted for STR - short term rentals VRBO then it might be worth it based on location.If you just want to buy a home and have a unit to help cover the mortgage I would still insist on lower price point or NO HOA to help get the total mortgage down so that the other unit covers 50% of the overall payment.  

I’m looking to buy a multi family property in Chicago, more specific in East Garfield Park 60624.

But what if you purchase with alternate financing (sub to, assumable (look at VA but requires OO), owner financing, etc) and only did buy, rehab, rent, and repeat (one less R - more precisely not a refi but maybe use 2nd or heloc)?

The current uses are: Production Industry - Artisan, Office, Office, 1br Apartment, vacant apartment, and a couple spaces that are not used by tenants.Thanks for the feedback. 

For example, if you are pre-approved for a $200K purchase, then you know that you can't buy in Nashville.

A paper trail allowing them to see what work was done while also seeing who did the work will deliver more polished products and accountability from all parties.

Investment Info:Condo buy & hold investment.

Given your expertise as a contractor, you might find an investor willing to fund the rehab in exchange for a profit share or interest on the loan.Cash-Out Refinance:If you own other investment properties, consider a cash-out refinance to pull equity from those properties to fund the rehab.I work for Aslan Home Lending and we have a HUGE variety of loan products, including the ones mentioned above.