But my understanding is that the majority of such properties in each major city are handled by a handful of brokers, and many never make it to the open market. 

Every lender has different standards on these as they are more of a portfolio product at the banks.  

I understand the importance of finding the right lender experienced with first-time investors/buyers and supportive of your unique positions as a business owner and W2 employee.As an investor, my network includes trusted mortgage brokers and lenders experienced in working with first-time investors and understanding the nuances of investment property financing.

Maybe some of you here who kept a day job but also generate income from investments can help me understands the basics of this.

- assuming 500hrs each, we have spent enough time this year to get to that but wondering if thats a red flag for IRS with high chance of getting audited (we travelled 7 times over the past year to work on the unit and spend at least a week each time excluding the time we spent managing the guests)- Lastly, our understanding is that each can take 50% of the final offset to our W2 assuming we prove material participation eligibility. 

What I want to understand better, is how many of you got into the game and got your start.

First step would be to read as many books or listen to as many podcasts as you can to understand both the buying process and how to identify a property as a good deal or not.

How do you go about accurately generating an annualized return % in this situation (I understand IRR is the superior calculation but investors like to know metrics such as equity multiple, annualized return, and IRR)?

I do #2 and #3 as they apply with a preference for rewiring.This exercise is helpful in developing an understanding of which circuit breakers control what.

Not sure If I am understanding your question fully?