I don’t know the individual personally, but the people I do know managing multiple units work 6- or more hours per week.  

Please judge our abilities and our integrity individually.

The house is rough, but we have experience remodeling and have a GC and an Amish crew ready to go. 

You can start a side gig to get some more income and experience. 

How was your experience?

So some basic numbers on these homes:Total estimated value of all homes including their primary home: 5.8MTotal remaining loans on homes: ~900kInterest rates on these homes range from low 3’s to mid 4’sSo two questions: 1) Do I need to cash out refi each individual home if I want down payment money or can lenders lend based on the entire portfolio?

Does anyone have experience with Subject-To deals in Chicago?

However, I aspire to reach your level of knowledge and experience, and be in your position soon.

STR's require immaculate staging, marketing, and appeal to younger, high-earning audiences who will happily pay $300-500 / night for a "unique experience".

In my experience, good design is good business; building something with character stands out to potential tenants (increased rent) and helps lower vacancy rates.