He specializes in sub to investing and can help you with the documents.

Mortgage brokers who specialize in DSCR loans can be helpful since they have relationships with DSCR lenders.

The bond market is pricing in the odds of a Federal Reserve rate cut (.25%) at 97.8%.But with inflation levitating - which is expected and which I do believe is temporary - there is still a chance the Fed shocks the market and does not cut.

They specialize in hard money loans specifically for real estate. 

Consider a lender who specializes in these properties.

As far as the process goes, it starts with having a good lender that actually consistently specializes in reno lending. 

For a renovated Pilsen 3-flat, somewhere $10–13K.Also check rent comps for new construction Woodlawn: if more buildings deliver, you may be competing through concessions or slower lease-ups.If it were me and I wanted a smoother first few years, I’d choose Pilsen unless the Woodlawn building is truly special or priced with enough cushion.Happy to run the numbers with you if you want to stress-test both deals, Chicago is all about underwriting the next tax bill, not the current one.

Just be aware of the filing requirements and possible taxes for each state, some states have franchise taxes or other fees for LLCs and S Corps.If you’re already paying 22% or more, an S Corp structure could potentially reduce self-employment taxes on any business income, but it might not change the tax treatment for the rental properties themselves.I’d recommend chatting with a CPA who specializes in real estate investing to fine-tune the details and make sure you’re not overcomplicating things.

You could work with a broker who specializes in high-risk properties or look at surplus lines carriers that insure wildfire-prone areas in California.

I have a 3-bucket portfolio with Total Stock Market Index funds, RE and cash/bond type funds.