Some charge me yearly others are 3, 5 or 10 years but I can’t think of a scenario this would work me unless I inherited a $500k IRA or really wanted to manage all these accounts & fees & IRS contribution & withdrawal rules or I took on a large gamble investment for a 30 to 100% return & got into active market again like flipping houses, etc.I guess I would rather pay the IRS less than a company like Quest IRA?

I think what Lucas is saying is you’re gambling if your game plan is to have a short term rental in a community of primary residents.

I have 15 years of experience in investing in actively owned real estate and 3 years of very immersed experience in passive investing in private placements and it is still challenging to source and select conservative opportunities (particularly in today's market).  

So basically I'm gambling on appreciation, with crappy tenants, asbestos, etc. 

Or, am I just gambling with the appraisal fee and hoping for the best? 

It's been a great learning experience with several healthy headaches, but I'm definitely ready to make a move into a larger home with central AC as Texas temps break the 100's way too often.On the profession side, I spent the past 7 and a half years in insurance, and in mid-2017, I began saving up for the jump to real estate so I could immerse myself in the industry (and hopefully pick up a few good deals along the way).

I have no worries about gambling my time over the higher probability it will close. 

And even if you do, there is always a level of "gambling" involved when dealing with these properties.Disclaimer: While I’m an attorney licensed to practice in PA, I’m not your attorney.

@Armin Trepic my advice would be two fold. 1) Having a knowledge of the stock investing, I am assuming you have a risk tolerance level as well as ability to think long term (investing not gambling) .

Have to hunt or take a bit of a gamble.