One idea I have is to "shadow" a real estate investor (although I am not entirely sure how to go about asking for / finding this kind of opportunity), but I am wondering if anyone has insight into other ways to gain a comparable level of experience.If anyone has insight into any or all of these topics, I would greatly appreciate the feedback.

I have a friend who also invested with this guy and she's received some small payments irregularly, but a small % compared of what she invested.I'll follow up on the items you mentioned to take action on, I appreciate the input!

I would offer 90% of the market value. if he sells it you with no agents he is saving 6%~ on real estate agent commission and the other 4% is a convenience fee in that he dos not have to endure showings etc. and you will get better pricing on a non-owner occupied property if you put down 25% is compared to 20%.  

I also look at comparable properties (comps) to estimate the property's value after repairs.I currently don’t have a real estate agent.

This is especially helpful if you plan to continue investing and don’t want multiple mortgage loans affecting your credit report.Streamlined Process: Since DSCR loans are focused on the property’s cash flow rather than personal financials, the approval process can be quicker and less documentation-heavy compared to traditional mortgages.If you want more info or need help getting started, feel free to reach out!

My thoughts- Pull comparables for other properties that have sold across from multi-families in the area. 

You need comparable sales and there are typically not a large number of 4 plex in close proximity.

You might put down 10-20%, which can be easier to manage compared to traditional financing.A motivated seller can be open to different terms, especially if the property has been sitting for a while, so just be creative and make sure the deal works for both sides.

A simple 5% return per year gets you $50k/year...and you still have the $1M to adjust to inflation by reinvesting into different vehicles along the way.Focusing on taking the long term returns ($$$/year) can be a better choice, but you have to look at the long term impact with all your options, compare them, and then make a choice.Do you think they teach that in school now? 

The appraiser looks at the sale price of comparable properties, the size of the property, and other factors that may affect its value.Home inspection: A home inspection is a comprehensive evaluation of the property’s condition.