The issue for you is you (or your wife) now may have two insurance carriers fighting over who will pick up coverage (assuming your intermediary LLC has appropriate insurance) or if it does not, your property insurance carrier may try to get out of coverage because of your slick deception tactic of using an alter ego which is the last thing you would want.Just  yesterday another BP forum poster wanted advice on a similar strategy when leasing a rental cottage on the same lot as their residence.

We're picking up extra work, multiple side-hustles and cutting living expenses... what am I missing here?! 

Picking a house with major, costly structural issues or in a location with poor rental demand can hurt both the rental and refinance phases.

Try some Ohio REI meetups or social groups—you’ll pick up a lot.

Pick an option then execute. 

Turns out, the demand for renovated homes actually picked up, since many locals were looking to move into places without the hassle of dealing with repairs themselves.From what I've heard, Tampa's market is showing some strong signs of resilience.

Have you picked a market and strategey yet?

After the election and purported rate cut(s) from the FED, I expect buying activity to pick up rather noticeably, which means more competition and likely higher prices. 

You can pick up some scraps, but it will be tough and intermittent.

Are they picking window style and placement, exterior cladding, color, etc?