I chose to invest most of those gains into a trucking company due to the lack of patience at the time and my 10 year experience being a tractor trailer w-2 driver.

Let's look at your example of a roofer, assuming he owns the company.He has to pay for employees- they still get paid, even if they are not giving 100% effort.He has to pay his workers to go back for warranty work - effectively paying them to do the same job twice.He has to pay for equipment, even when it's not being used 100% of the time.- but the company he bought it from still gets paid.He has to pay for advertising, whether it works or not.- but the advertising company still gets paid.He has to pay for accounting services, payroll services, tax services, legal services, etc.- they all get paid whether he makes money or not.So, what's your point?

Sure, it can be quite a process, but with experience and a growing network, it does become more manageable.Let's go!

Does anybody else have experience as of lately...? 

Quote from @Shaun Ortiz: Hi Jason,Thanks for sharing your journey—it sounds like you’ve gained some invaluable insights from your experiences, even with the squirrel tenants (that’s definitely a story!).

I have an idea of an initial investment and returns I would like to hit, but would love to speak with those of actual experience to see if my numbers are realistic.

I'd be interested to hear others that have specific experience with them. 

highlight_post=5222888&page=1#p5222888https://www.biggerpockets.com/forums/311/topics/915728-experience-with-rent-to-retirement-turnkey?

@Wiley Hood DIY cost segregation tools like KBKG can be cost-effective for simple properties, but they lack the precision and audit defense of professional studies.

I have over a decade of experience in strategy consulting and in real estate underwriting for new acquisitions and ground up developments.