The flippers we personally work with in California have not run into this issue (as far as I'm aware).

Having graduated from BC myself, I understand the charm it holds, which can be perfect for the right person.

Take into consideration that when the person you gifted the property to will have special tax considerations as well 

Do you own these properties in your personal name or through an LLC?

BUT, let’s say for personal reasons you want to “stretch” for faster wealth accumulation.  

While this job could be performed remotely, working with my peers in person for at least a year is important to me.

I've done enough personal home projects to know, if I find a deck company it'll be 2k, but a GC will charge me 2.5k to over see it...

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

I personally think it is best to work with local professionals with a good track record. 

Keep in mind, you can’t use personal funds or your home's equity to directly fund the SDIRA investment, and all property expenses must be paid from the IRA.