Building a strong team (agent, contractor, lender, property manager) is key—seek referrals from experienced investors.

If numbers work and risks are manageable, this could be a solid house hack!

We live in Northern Florida and manage our 10 long term rentals and do flips in northern Florida and we decided not to go that route with this south Florida home after we started digging into it.  

I'm a lending manager with 120 loan officers under me and 2 of my great friends and colleagues specialize in manufactured lending The reason most lenders don't do them is because:1.

This is a question for your attorney and accountant on how you will manage the company etc.

That brings us to 2- the ability to negotiate to CREATE a good/great deal3- financial staying power (being able to survive when things go south)4 - property management 5- creativity 

I've learned a lot on the managing side of the business, as well as the rehab side DIYing a lot of the work myself.

Managed and renovated entire triplex in a newly revitalized area.

You need a reserve to handle unexpected costs, particularly during the first 1-2 years of ownership and learning how to manage the property. 

If part of the property is rentable while renovations are happening, that could help offset carrying costs.Given your construction background, you’ve got a huge advantage in managing the project efficiently—it’s just about getting through the red tape and de-risking the unknowns before pulling the trigger.Have you talked to any local investors or contractors who’ve tackled similar projects in Wicker Park?