I see it as no different from borrowing from a bank.

If someone came to me looking for money and was trying to invest across multiple asset classes as different as the ones you are interested in, that would leave me extremely weary.

If you have other money besides the 20K then this is a different story

Hey @Michelle Baldwin, yes this is a challenge but everyone said it best.Simply, you can just use a different browser to be logged into each VRBO account.I also think that @John Underwoods idea will work as well.

Every job I see requires 3+ years of experience and knowledge of multiple different programs.

The only difference is that the sold property was not updated. 

First red flag is if they say that they will shop your deal with a few different investors.  

This matters as different auctions are prone to different title issues.

Some lenders will also have seasoning requirements for the loan itself, which may be different than what's required for ownership.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?