I want guaranteed monthly rents because when I purchase my main focus is cash flow, then equity in the form of added value (renovations, adding extra bedroom, etc).

Be smart about what package you choose to purchase. 

Purchase price: $726,000 Cash invested: $1,300,000 Sale price: $4,500,000 We are developing a 4 story a luxury Duplex.Property is primed for short term rentals with conservative estimates of ($40,000-$50,000) per month.

We currently own one door (split acquisition and closing costs and contribute equally to management and ownership), and have split equity and cash flows from the property - also pretty standard in my experience.My question is this - I want to purchase a house hack and would like to use our current business entity for accounting purposes (tracking income / expenses / etc).

I have used DocuSign for selling and purchasing agreements, but not for closing. 

I am looking to cash out refi here soon to pay it off and use again to purchase my next rental property.

A third party likely purchased that debt from the original lender (uncollectible by typical debt collector standards) for pennies on the dollar. 

I am going to try and remote self manage and see how that goes but if it is tough I may use them for my next purchases.   

Have you considered purchasing a 1-4 unit as an owner occupied and renting out your current home?

At a $65,000 purchase price, with a 5% 30 year mortgage, PITI comes to $700/mo with rents bringing in $1750.