A lot of these southern beach & mountain towns have been supporting STR for 75+ years, long before Airbnb was a thing, so they’re very comfortable with it and it’s a built-in part of the community.A lot of Northern places are FREAKING OUT over STRs & STR regulations & they don’t seem to be very supportive of it.

Many out of state markets cash flow but it all depends on your comfort level as to which one is best for you, there are big differences from SoCal in some of them.

All of the processes afterwards I'm very comfortable with (just need to get them in place for when the time comes) - market knowledge is where I have some ground to make up!

For the fist time I feel like I have the knowledge to be comfortable and confident in taking action, and I have a better understating in all the investing perks of real estate, it’s only made me more hungry to do this.

I  used to think cash flow and numbers are paramount, but as I have aged now 64 I find that I am willing to sacrifice  a little cash flow (not a lot) for the ease and comfort of managing my portfolio.  

One of the reasons I'm not a huge fan of annuities is that they are so complicated it is hard for clients (or myself) to understand them fully.If I were in your shoes I would call the annuity company and ask them to explain what each of the values in the statement mean and what you should expect to receive.You'll probably want to stretch the IRA over your life expectancy.

I'm aware of PMI, it'll need to factor into my numbers.I told the guy I wasn't comfortable paying for coaching at this time, and his reaction was quite surprising.

A lot depends on your comfort level. 

@Ryan DaleOh most definitely that’s very similar to me except I have not worked as long as you in other careers so I am not yet financially able to start any investing YET, but I do plan on learning the industry inside and out to the very best of my ability so that in the future when my financial standing will allow it I can invest with as much comfort as money can allow within reason.

Just so I get versed and feel entirely comfortable when speaking with potential clients.