Having someone like that in your corner can save you from costly mistakes and speed up your learning curve.On the other hand, if you already have a firm grasp on the process, understand contracts, know how to analyze deals, and have your own relationships built out, then handling transactions yourself can make perfect sense.

my recommendation would be get a bridge to dscr, and certain lenders will work with you to not charge points on each transaction if you go through them for both transactions.

Their website says their platform is completely free. Has anyone used it before? How do you like it?

Pull recent cash transactions in PropStream or Privy, check the LLCs or buyers behind those deals, and give them a call to see what they’re actively looking for.

Property management in Chicago is no joke...I highly advise against getting into it, lol, unless you have some crazy competitive advantage, which maybe sounds like you do.We've got a small brokerage team, most of whom do not transact heavily and do some investing on the side. 

It's not private money but Mach1 Lending is very well respected in the SEWI market as hard money lenders who are more like partners in the transaction (not in an overbearing way...but easy to talk to, helpful).  

For most smaller investors, paying for a solid bookkeeper would generate a higher (and faster) ROI than hiring a tax strategist.Both roles matter, but you can’t execute any meaningful or complex tax planning without clean books.

It may be worth spending 5k-10k on a transactional real estate attorney for this. 

I would probably get a buyers agent to represent you in the transaction. 

The seller wanted a straightforward, as-is transaction.