@Eric Lee Nation There are a few changes would recommend you consider.1)  Remove the Med Pay (if possible) and putting hat premium towards a higher Liability Limit

In my limited experience I would say that if you go virtual in a different market (say a smaller city with lower priced homes) you'll generate more leads, but you may struggle with disposition as there is less Investor activity from your potential end buyers (Small,Med, and Large Flippers, Institutional/Hedge Fund Buyers, Turnkey Operators..etc) On the flip side if you stay in the more competitive market it will be a grind to get those first few leads and to secure a contract but your odds of not being able to dispo it should drastically decrease (Assuming you have a discounted deal in the right area) and that check should be NICE. 

@Chelsea Ziss As mentioned, you need a cpa”s advice going forward.But...1) do not put the rentals in the S Corp.2) it Could be beneficial to do your flips, depending on how much you make per year with flips, in the S Corp3) your flip profits are not capital gains, they are ordinary income and just like your commission 1099 income, subject to 15.3% ss/med self employment tax. 

Has anyone dealt with tenant who is bipolar, off their meds?

@Kunal Patel If you have “non employer reimbursed, deductible expenses” it would get deducted off your income for federal income tax purposes....but you would not get any deduction/rebate for the 7.65% SS/med which your employer withheld on your w-2 income. 

To echo what others have previously mentioned, Option 3 is out of the question since it's a low/med income area, so renters in this population would most likely not spend for a washer/dryer.

A mental hospital called me on his behalf because I threw away his meds.

I'm thinking a med student in a 3 year residency would be ideal. 

They do not require that a homeless person becomes clean, sober, or takes their meds if they're mentally ill but puts them in a house. 

If you paid your llc, disregarding your son and his lower bracket, your expenses/write offs would be no different, but any “profit” going thru your llc would become taxable as ordinary income (with SS/med taxes) as opposed to the passive rental income it is now.