I’m inclined to send them a note demanding fair market rent for the last six months and then filing failure to pay paperwork if they haven’t complied in five days.

Covid-19 has probably made this strategy a little more challenging due to people being less inclined to live with a bunch of roommates right now, and occupancy limits for non-related residents is also something to consider with this strategy, but it can be a great way to maximize rent in a single family home that otherwise wouldn't provide cash flow.

For this reason, and the fact that my wife would rather live in a single family than a unit in a multi-family, I am inclined to single family. 

If you are doing the appraisal through the lender, you might be more inclined to just take the deal :)But yes, you can always get a 2nd appraisal.

The more research, reading and connecting I do the more inclined I am to go with the house hack.

That said, I am inclined to get a property manager anyway for several reasons.

I'd be inclined to think the opposite - that rent will grow more on a SFR than a MFR (on a per unit basis).

I feel inclined to say no unless the rates are really worth the potential hassle. 

Personally, I'd be inclined to sell it, though having a pool that is not operating is only going to appeal to a small subsection of buyers, likely all investors who will want to low ball you.

You are more inclined to pay higher dollars for property if you underestimate the expenses which will VERY rarely be under 40%.