anyone have a lender that is STR/second home savvy? 

I did a pretty conclusive poll of about 14 lenders of all sorts and each and every one wouldn't allow larger loans for operating STRs.

Interview a few professionals and get proposals to compare.   

Does anyone has experience working with "The Lender" to finance a short term rental property?

There is more that goes into it but you are essentially a middle man.For fix and flips you don't need a credit if you make relationships with asset based hard money lenders.

Gross income is easier to establish and this mirrors how lenders qualify buyers for mortgages.

I would work with an STR lender before construction to verify that a deal will be eligible for refinancing.

It normally comes down to- improper sales comparables analysis- bad contractors

DSCR loans are a great option for anyone that doesn't fit the conventional "box" - DTI isn't a factor, no employment info needed, no W2s, paystubs, tax returns, 1099s, etc. needed, you can close in an LLC if you want to and many lenders don't report to personal credit, so those loans won't affect your credit score/DTI for any conventional financing you might pursue in the future.

There are some foreclosures if you have $20,000,000 in cash or maybe you let the lender take those back, but then you get class B office with 50% occupancy.