Keep in mind that if they buyer (borrower) decides to pay you off early it will trigger the deferred taxable gain.  

Is it possible to buy a home under your name and transfer it to an LLC without triggering the “due-on-sale” clause?

My biggest question however is: when will I know it’s right to pull the trigger on a property?

@Joe Splitrock, as far as we can tell 1031s of any type are not an audit trigger. 

I appreciate the opinions, I’m not sure if I want to pull the trigger or not.

Weird things can happen (COVID), so don't bet the farm on every project or go for properties that are too high ARV or out of the neighborhood norm.I'm hoping my experience can help some others either pull the trigger in fix and flips or at least provide some entertainment. $1,050,000 - Purchase Price - funded by 3 partners in cash.$415,000 - Total Cost (Renovation Costs)$185,000 - Commission/Taxes/Fees/Escrow/Holding Costs (Took 1 yr 4 months)$2,000,000 - Sale Price$350,000 - ProfitThank you BP community for always providing help when I need it and sharing knowledge graciously. https://www.redfin.com/CA/Berk...

For example I almost pulled the trigger on a duplex last week.

I think you are right though, I just need to find the right deal without needing the funds out of pocket and that will force me to figure it out, which may take me the time we've agreed upon to pull the trigger.

I'd love to talk through any Missoula deals with you, whether they're potential or ones you've pulled the trigger on. 

Learning is so much easier today than it was 10 years ago, and there are amazing educational resources, financial resources and professional feedback resources that ease the stress of "pulling the trigger" on a real estate investment.