If we knew we could get her into one of the good charter schools (lottery system, so pure chance to get in I guess), we might just look at a simple SFH and stay there until we die or downsize later in life.

I personally just like for government to stay out of my business as much as possible so I hope that STR are allowed.

Not that it matters but I am a stay at home mom gathering money to invest.  

Inventory stays forever on the market in smaller markets and if you're going the HML route, the interest costs will eat into your profits in no time.Don't view a market as expensive or cheap purely based on the average price of a property.

I asked the typical questions (is it staying cold, shutting off, leaking, etc.).

With all current comparable of 2/1 in the area with same sqft is around $385k-$400k, I converted to 3/2 with permits our contractor and I ran into many challenges with the city inspection and also tried to stay within budget.

But there's restrictions put on realtors and that's the main reason I've stayed away from it. 

I would likely stay here and rent for another ~2 years then move out of market.

As long as all tenants are staying in place, I do not see the point in rekeying.

After all, when the economy dips again (which it surely will), these homes tend to stay rented with much lower turnover.