It sounds like you MAY have been postponing a (legal) confrontation with some tenants due to fear.  

That was when the stock market was depressed and there was a lot of fear. 

In fact, vacancy and tenant damage are two of the largest fears of most investors.

My fear is that for some reason it won't be reclassified back as a multifamily, or that during the assessment it will uncover some other thing requiring costly improvements.

I feel a bit overwhelmed jumping into real estate investing(even though I know this is what I’m going to do for the rest of my life) I just have a lot of fear about diving in with the first deal.

Its a mixed bag but you will have the benefit of government paid most of the rent,  and the tenant at least will have the fear of losing their subsidy to help keep them in line.   

If you have a good reason to go to a location don’t let the fear of leaving things behind stop you!

My wife and I have been interested in RE investing for some time but have stopped ourselves due to the overwhelming fear that comes with going into the unknown.

Be Fearful When Others Are Greedy

And by rule abiding nancies I mean limiting and restraining themselves and their agents with undue interpretations and fear.