@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. 

Small - Med - Large?  

Yes, they are taxed as ordinary income (doesn’t matter if this is your regular business or not) plus SS/med tax of 15.3%.