Now filing for 2018 tax, first Question: should this house go on Schedule E again ( as if it's not sold) and all losses are deductible on Line22?

I can't deduct the interest on a HELOC on property 1, to fix up or improve property 2. 

It’s a great way to learn about deductions.

The tax code is set up to give out all kinds of deductions.

If you purchase as investment and you need to cash out in order to get the funds for down payment, I suggest a regular refi and not a heloc, rate will be similar with the purchase and definitely better terms than a heloc, also Heloc are riskier, they are not governed by the Fannie and Freddie, you are not as protected, also as this year, you can no longer deduct heloc interest on your taxes. 

However, tax deductions work differently when they are attached to rentals vs flips, and for clear separation I would still recommend LLC 2.Your idea to offset flip gains with rental losses will not work.

Keep looking for deductions but the wisest thing to do is to stop the charitable deductions and use that money to pay your taxes.

Each property is running me around $1400-$1900 per year in premiums with a 1% deductible for RCV coverage.

One being, using it for tax benefits through cost segregation where one reallocates assets in a property to personal assets and it allows owners to take accelerated depreciation.For example a $2m building with negative cashflow can mean a $500k depreciation (and tax deduction) on year 1.

hi, I recently bought a small 7 unit building, and the super is getting a $500 deduction off his rent, I was sure for that hefty price he does EVERYTHING  in this small building, so when a tenant moved out I asked him about painting the apartment so I can rent it out, he said he would need extra payment for that.So basically what it sounds to me, He basically just does the garbage, snow, cleaning (not to mention that is not too clean, spider webs on ceiling of entrance etc.), if you need to change a lock he'll  do it etc.