She’d be adding a guy to the lease she’s been dating 2 months and if she doesn’t, does that mean he wouldn’t be allowed to visit or not as much?

Expenses and capex seem screaming low.

I would agree and urge you to start easy with a SFH, UNLESS you can find a screaming deal on a MF, then just jump in and figure it out..... :-)

He flipped a switch and started yelling and screaming,stating he was a protected class with military rights and he would take me to court, etc etc.

The markets may slow and inventories grow again, but Americans (and foreign visitors) will not stop vacationing. 

Ironically this most often happens with people who scream “ this is a business” most loudly.

Another alternative is looking into surrounding towns, like Oak Park or some other suburbs that might attract short term visitors.

Dishwasher gap looks cheap and screams "cheap place".It needs to look more expensive than the asking price.Allow dogs - pet rent, extra security deposit.I disagree about lowering income requirements or background check However, the security deposit is high for sure.If the price is right for the market, why the property is sitting since May? 

Some markets will keep going up then you will scream why did I not buy.

In my research, it appeared that DHS would be less desirable to visitors.