You would need to bring everything up to code currently and that's going to be cost prohibitive.

We are currently building many investment Single Family Homes on independent lots that focus on maximizing rent.

I hope with this extra info you can see more clear my current and future goals. 

You’ll need to thoughtfully evaluate the timing for flipping, renting, or bundling properties for bulk sales, all while considering current market conditions and your financial objectives.Balancing Flips vs.

In high-cost markets like Chicago, that can be tough to meet.If you're looking at a duplex, the self-sufficiency test doesn’t apply, so you’d just need to qualify based on your personal income and the rental income your lender allows.If your current lender isn’t familiar with making FHA work in your situation, it might be worth getting a second opinion from someone experienced with FHA multi-unit financing.

Quote from @Gabriel Williams: Been listening to BP for several years and I’m currently working on our 5th deal.

I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.

After that's under control, focus on increasing income through additional work at your current job, taking on a side hustle, or finding ways to increase income on your existing rental.At the same time, educate yourself.

We currently have fixed interest rate at 2.85 on one home and 3.25% on the other 

Quote from @Victor Yang: If I gift a house, what amount will go towards the lifetime gift limit, the amount i purchased the house for, or the current FMV?