Looking for a way to up my game.  

Your payment should drop by two thirds.$160,000 for a 2,000 sqft house is cheap, even for Milwaukee proper.

I'd like to your feedback on two options I'm considering.

In a wholesale transaction the seller is in some kind of financial trouble which the wholesaler is helping to resolve.You have two options an assignment or a double closing:I haven't done an assignment myself so not sure completely of the process, but in a double closing there is already a contract with the seller and the wholesaler who is fixing the liens on the title, when that is resolved there is a closing date where the wholesaler execute the contract with the seller and you execute the contract with the wholesaler.In general the closing cost in these type of transactions are covered by the buyer which it could be around 3.5% and it does not include sales agent fees.There is one thing that I didn't understand, it seems that the hard money lender is in charge of the transaction.

I hear that can be difficult securing lending on two owner occupied properties in the same town / area.

They reached out to me two days later and said they weren't able to contact her via phone, text, or email.

$1,400 x 12 months x 5 years = -$84,000.Net Worth ROI Calculation (new situation):Appreciation: $108,280Loan Paydown: $31,807Tax Benefits: $0 (b/c you aren’t cash flowing)Rent Avoidance: -$84,000Total Net Worth Increase: $56,087ROI = 56,087/25,000=224.35%Simple interest rate of return = 18.7%/yearHouse hacking can be a great way to build wealth and get into the real estate game.

When looking at an LLC, or any entity structuring, there are two angles to consider: tax and asset protection.  

Perhaps knowing as much as I know about risk has made me a bit too risk averse - but I am about to step in the game and give it everything.More than likely, I will focus my efforts on Indiana and very likely Indianapolis in particular, but I am also amassing intel and remaining open minded.

If I knew then what I know now, I would have started much sooner, as soon as I could get any kind of downpayment.I would have bought a small home or condo with two or three bedrooms.