Of course back then we were getting “screwed” with 6-7% rates.

Imagine making millions of dollars over the course of your career and then having to pay 30-50% every year to uncle sam instead of compounding that cash over time.This is exactly what real estate professionals have learned to mitigate.To reduce their taxable income, they just buy a building every year, do a cost seg, and use depreciation to reduce their tax liability dramatically.Their personal wealth snowball grows much larger and much faster than their W2 counterparts who give most of their money back to the government each year.Following this strategy as a real estate professional is one of best ways to end up with a much larger net worth at the end of your career.

He pockets the downpayment to cashout what little cash he puts into the deal and then makes the spread between the two loans.

In other words - if you do not cashout refi either the new property after rehab or the existing rental, then where will you obtain $100k cash to pay off the heloc? 

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

If you're a landlord, then you'll want to educate yourself on the local laws.

Building a team is something after you build the skills yourself, then teach them to other people to leverage more and more.

Then you have the ability to accept or reject their response.4.

Then look at different REI to scale to that number.  

We have thought about making the 3rd unit an Airbnb because then we don't need a full kitchen.