This contractor has 0 reviews on yelp which I found a bit sketchy, but was able to vet him by his contractor's license, worker's comp, and by visiting some of his ongoing projects.

I think the only time they would question me is if they suspected I was doing something illegal.

Likely just raising it above market rent would be considered stupid, not illegal because then you’d have a vacancy.

:- As others have noted, it's a slow time of year... if you and your husband are open to it, it might be worth listing as a 'mid term' rental for a few months (for traveling nurses, gov. contract workers, seasonal workers, etc.) to get you back into the prime renting months of Spring/Summer where you can resume looking for LT (12+ month)  tenants.

Two Reasons: First, because 50M people in this country either work gig jobs or are illegal immigrants, when they lose their jobs or have their hours scaled back, it doesn't show up on official unemployment stats.

As a beginner, you can learn a lot from your uncle with a few rentals in another state or a co-worker who's on their second house hack.

If forced to cure - and it will be a condition of remedy - the tenant can take action against you for damages from leasing an illegal property. 

@Jessica ZolotorofeHello From the Future ;)Ive spoken to a couple title companies, and transactional lenders and I have not heard about double closings/backtoback closings being illegal.

IMO Most of the time, people lose lawsuits or settle for much less due to laziness and lack of rock-solid knowledge about the illicit/illegal acts the opposing side committed.  

It doesn't sound like you actually have an illegal unit here.... you have a two unit with a garden.