It sounds like you’re aiming to offset your W-2 income with potential real estate losses, which can be tricky if you don’t qualify as a Real Estate Professional.To qualify as a Real Estate Professional, you or your spouse need to spend more than 50% of your working hours and at least 750 hours annually on real estate activities.

You should consult with a qualified contractor to discuss options and costs for proper repairs.

Being self employed then too, I would not qualify so I never started that way (and I was very young (like 23).

How does one go about making an offer on a commercial space that is becoming vacant shortly, such that if I cannot find a qualified tenant to fill the vacancy that I can walk away from the deal? 

Find out what you qualify for from a loan officer or credit union. 

I am looking to purchase a property that falls under the minimum limit for DSCR but qualifies for a conventional loan. 

Hello, You can purchase this as an investment property, using the DSCR program, where we simply qualify the property with out using tax returns, etc.

Now that you have a signed lease (assuming it's 12mo+) you can use that income on your taxes to help boost income to better qualify for a multi-unit.

Hey Bryce, You can use AirDNA rents to qualify for STR DSCR loans instead of showing 12 months of short term rental history.

Option 2: I found a house that the asking price is 930k , but I’m sure I can get a discount on it because it needs a lot of work , it doesn’t qualify for traditional financing , so I would need to take a hard money loan , it needs about 150k worth of work , the plan would be to offer the full 930k asking price but ask for a 6% seller concession , I calculated 20% down payment and 7% closing cost , so total after seller concessions comes out to 21% down payment which is $195,300 .