Debt is rarely a factor in their issue. the ultra wealthy I know  with a few exceptions have very limited debt.. to no debt. 

Unless Quickbooks has addressed the issue does not have a specific real estate module so you have to work around it using customers as properties and jobs as tenants.

Customer Service integration to handle tenant issues, monitoring of Mechanical issues where the A.I. can proactively do something to ensure it's well maintained or to be able to fix an issue, etc.My Portfolio has basically been self-running except for occasional P.M. 

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

The reality is there are many issues with ADUs as an investments and the poor valuation is just one of them.  

You’ll want to get loans from local banks and credit unions but you may run into issues with more limited features.

Your issue more so is the seasoning period for the refinance is what it sounds like.

I know I know getting property won't be an issue, I've done it once and that experience helped me so much, but what if i wanted to acquire two properties this year?

We distributed profits to investors quarterly and returned a 45% IRR to investors annually.

The biggest issue with Stessa is that it sounded like they had very low transfer maximums(making it difficult to pay people) but it looks like they've improved a little bit on that.