Let's jump right in.The Power of Short-Term Rental Tax Strategy:Short-term rentals offer a unique opportunity to offset your W2 income with real estate losses, thanks to an increasingly popular STR tax loophole.

Tenant estoppel letters should be used in the sale or purchase of any tenant-occupied real estate, whether residential or commercial. 

(Does any other wholesaler have a stake in this sale as well as you?)

Congratulations on the sale.

Quote from @Sarah Rhee: I have a real simple rule for investing: never sell an investment unless you can move the money to a better-performing asset, or if the sale will move you closer to your goal.Your situation doesn't meet my rules.

I am not not super familiar with the auctions or sheiff sales, but if you are interested in NW Indiana consider connecting with @Eudith Vacio who has some property in East Chicago, but works that NW Indiana Coordior and is a top agent!

First, see if you can negotiate replacing the sale contingency with a longer escrow or loan period.

- What are some methods for projecting cash flow from home sales and determining an appropriate discounted cash flow (DCF) rate?

For a standard 3/2 with 1,200 sqft we usually spend 50-80k on a full rehab, 10-15k holding cost, 15-20% profit before tax, 7% cost of sale.

A CT licensed atty will need to be used to close the sale of the property.