With excellent credit (800+), you're already in a great position, but I understand the struggle with DTI when you're self-employed.Here are a few options that might help:Asset-Based Lenders: You're on the right track with DSCR loans, but you may find some private lenders or portfolio lenders willing to go into the high 6’s.

Hey there,I'm interested in utilizing private money lending for financing while I save up to use my own capital along with Hard Money Lending.

Private Money.

Please share your thoughts:What are some of the most favorable terms you’ve negotiated with private lenders? 

Also mother in law suites and private bath are not as available.

What I would do with the sale proceeds, as pointed out in your post, is reinvest in a first deed private money loan anyway.

What are the biggest challenges you face as a private money borrower?

effectively, you'd either need to look for a lender that would let you use the other property as collateral (cross) so that you can avoid actually taking the cash-out (this is rare in terms of institutional DSCR lenders, but fairly common in the hard money or private money space)...

because I'm thinking no one can really tell you when to sell your property, since it would be difficult to get a loan from a private/hard lender first off.

This would be better answered in a private setting with your tax professional to determine the best steps moving forward and structure.