If I could chime in to help in the search:be sure to find an accountant who is willing to grow with you, and is not too high priced fee-wise.

I highly recommend starting by tuning in to the BiggerPockets podcast for starters.

@David McFarland I second the comment that if they can’t pay the rent now it’s highly doubtful they will be able to pay it in the future.

My thought is that it's better to own fewer high quality properties than lots of cheaper ones. 

I'd love to share some insight I have gained in that regard from my time in Austin. 

What guarantees for success does it make and what outcomes are measured regarding the validity of the "program"? 

The triplex technically still has cashflow at the moment so I think I would be aggressive on the duplex then look at cash for keys in the triplex and get that done in one fell swoop. 3) Renting and Managing - While not the most expensive areas overall, there is demand in these areas from people paying at or above the top range I listed for high quality units.

I would also highly recommend you starting the loan process now.

I’m assuming that I’d have to personally guarantee the mortgage as the LLC is fairly new (18 months) and the cash flow from the property is not especially compelling given the current high interest rates.

Let me know if you have any particular questions regarding the Milwaukee market and buy and hold.