The tenant would like to know if I would pay or minus from the rent.

I am 33 years old and know that the money will be worth a lot more in tax free accounts in retirement.I have w-2 income1099 income (building side business for self directed roth 401k)I currently own no IRAs only a roth account.

Should I be saving my receipts when I attend local meetups for a tax writeoff?

You probably recoup the 5k in ARV, but Old North Milwaukee is an economically challenge neighborhood, so manage your expectations.Avoiding frequent turnover, tenants who don't pay, damage property or cause other issues is the name of the game to achive long term profitability.

You might lose more than the taxes if you’re in the 15% capital gains bracket. 

In this current interest rate environment, I’ve found notes (those underwritten well) to be doing very well and paying pretty consistently.

This is one of the many ways that PM’s pay for themselves.

Also, make sure your accountant knows how to add the cost seg to your tax return.

You're paying down debt fast and your not accuring much interest at all.

So all in I am at $240,300 , hard money I am factoring in as 15% rate and since I’m borrowing 840k for let’s say 6 months , I’m factoring in hard money costs at 63k for 6 months So now all in I’m at $303,300 ARV should be at least $1.3 million (conservatively) I would cash out refi with a dscr loan and get back 975k , I would pay the $840k I owe to the hard money lenders , leaving me with 135k , and I would pay myself back with that money , and since I would have $303,300 invested , I would pay back 135k to myself leaving me with $168k invested in the house with a equity position of $325k , the actual house number are such after the cash out refinance: This house has 2 units and 3 accessory units Mortgage : $7100Heloc payment : $1300Total = $8400Live in 1st floor Rental income 2nd floor : $30003rd floor: $1500Accessory unit 1 :1200Accessory unit 2 $1200Income : $6900 Net : negative $1200I also already have a house that’s breaking even , but I’m living in one unit and if I move out that house would become positive $1500 which I can put toward the payment of one of the other houses .