My main concern is the cost to furnish the homes is something I’m not sure I want to spend on.

Here is what I’m concerned about, i did all the work myself/ paid cash to get it done.Here are the upgrades(I’m sure some of these might not need a permit but I’m new So idk)-Added central heating and air -tore down two walls to make an open living concept (non load bearing)-renovated kitchen/moved gas line-replaced some of the foundation 2x6 floods became they where damaged by termites -add/move electrical sockets-new floating floor-replace pluming with pex/ pbc-painted inside-replaced a window- maybe more but you get the big picture.Will the appraiser report me to the city?

It made me concerned about the agents due diligence on the others.

The cashflow is decent as a midwest city, and there are some really nice suburbs as well.I'm mostly concerned with the future of Chicago, and if it will continue losing population, or if things are expected to reverse/ level out over time.

If concerned lay Luan down first for a smooth finish.So...for all the selections at LL I'd choose a grip strip over the click variety. 

Not sure why the seller’s agent would have any concern for what you plan to do with the property after you purchase.

@Tina Rubin as an occasional lender myself, I think the second option (new deal/property) sounds a little cleaner and more of the traditional lending scenario - if I’m understanding you correctly.Just make sure you have a good understanding of the higher rate you’ll be paying to the HML and make sure you can still make your numbers work with that higher payment amount.A hard money lender’s main concerns will be the value of the collateral relative to the loan amount (LTV), and whether your estimate of the project cost is accurate.The HML will definitely want you to bring a substantial amount to the table as a down payment to keep their LTV low (65-70% is common), so if you need to refi your current property to get those funds then that might be something you’ll need to look into.If it was me I’d probably stick with a traditional fixed loan on the first property and start out with a private/hard money loan on the second, until it’s rehabbed and stabilized, and then refi out with another bank loan.

@Jillian EzMy CPA told me to talk to a real estate lawyer for the best answer, but offered this:“This depends on several factors including concerns for liability and budget.

It's hard to say what your wife's true underlying concerns may be.

@Wayne Brooks i understand your concerns, yet I have a a lot of friends that flip homes, friends whom placed the interest in me to do so.