Your cost basis would be ALMOST zero if you ever sold.

If that's the case, you should be able to rate/term refinance at ~75% LTV with a DSCR loan, and with some interest-only basis, your payment will go to ~$850 (based on ROUGH pricing TODAY).

I live in Honolulu currently but used to live in Tokyo (mother is Japanese) and still travel there on a regular basis (pre-Covid).

If you're buying it shortly and THEN after you own it will it be ready and available for rent-the costs will be capitalized and accounted for with the basis of the property as well (when you eventually buy it). 

As fund manager you owe your investors a fiduciary responsibility which I can foresee as a basis for lawsuits should the fund not perform as anticipated.  

Or, is it better to look at it on a per investment basis.

I do all the expenses (simply because that is easier than me communicating with Bookeeper every time I have a charge) and she does inputs on monthly statements, balance tracking, basis, loans (7 loans), and reconciliation. 

@Jacob Dalton, I'm going to have to agree with Jonathan Klemm (sorry, couldn't tag you) & @Brie Schmidt -- you can definitely be a successful landlord in Chicago with the right team in place.  1000's of investors do it every day. 

Also, for the variable rate, that can sometimes be mitigated by caps in frequency and/or basis points.

If I got a home equity loan for Property 1 and used the proceeds as downpayment for Property 2 and then got a 2nd loan for the remaining 75% purchase price for Property 2, when I sell Property 2, can I use the Property 1 loan as part of the cost basis for computing Property 2 capital gains?