I have personally been the guy who hasn't pulled permits and got caught...by far one of the worst experiences of my investing career.

But in this case, all the proceeds of the sale of the first property go to you, and you are able to bring the entire proceeds of the sale as a down payment on the second property.

This is a very long discussion and would need to ask a number of questions - we work with investors from many different countries. 

I know that my current cash flow is a result of the unit being my primary residence first, and that not all units will cash flow like this, but can't help the feeling that I should be expanding my rental portfolio over the years.

we ran into this in FLA  a few years back when I had 4 starts and I exited that market.. permits  sub base all pretty tough for someone who is not there and already knows the systems hands down and has a devoted loyal sub base.. thats the key in my mind.

I think that Chat GPT hilariously acknowledges, however, that if this person then goes on to run for governor of Colorado, then, despite their likely lack of time and attention to the money I put into the investment, that they are likely to put up phenomenal returns as a nice bonus of either being in office, or being a threat of attracting any meaningful percentage of the vote in that state before dropping out and endorsing an eventual winner.

This means that the bulk of the expenses are not going up annually.In addition, if OO you get to write off the property tax and interest to the SALT limit ($10K). 

I'm in the process of transitioning out of Cozy due to the limited functionality and my dissatisfaction with the apartments.com merger.  

.: Quote from @Tom Gimer: You can't take an element from state X such as "uniqueness" and try to apply it in state Y where that appears not to even be part of the analysis.Let's see how this turns out. 

Every time you lower your tax bracket you are lowering the value of the deductions.