My definition of retirement is having enough income to pay all my bills/expenses without clocking into a W-2.The rentals require management, which I do myself, and if I want to experience more—say travel the world, or buy a nice car or a giant clawfoot tub for my wife—I have to find more cash to fit those things in the retirement budget.As for an account that pays for occasional repairs, if you can find it, there are companies who will give you HELOC Sweep accounts on as many as three properties combined.

Does this give the STR a more professional look or do travelers prefer to deal with individual hosts? 

@Joe Splitrock when I recently got an insurance payout from Travelers they paid me via Zelle.  

The girl friend said that the father if very busy and travels at least 6 months out of the year and wouldn’t be here at the property often.For me, red flags seem to be popping up all over the place.

I mention this because I work for myself, have no W-2, and won't be able to get a conventional loan.My future plans include continue traveling around the U.S. in my RV, buying an airplane, and continuing my flight training. ;)Any advice on what my best 'first step' might be?

Travel ticketsThe trip is domestic and primarily for business, so his travel is 100% deductible.

Remember you'll be tied to the place you buy property for the foreseeable future, and you need to be comfortable interacting with that place continuously, at least in the beginning, probably traveling there but at the very least virtually/ by phone. 

We have two young daughters (7, 2), and our goal is to gain financial freedom and independent wealth so we can travel regularly as a family and pursue a number of passions we've had on hold.

I feel that some people who boast about their appreciation right readily forget the losses they have incurred- and I also can't imagine a way that they could ever be properly quantified.One thing that I know is that to the extent that my buildings or business takes time away from my family, it pays for immediately, monthly... promptly allowing us the ability to travel, enjoy recreation and still have a large chunk to elevate our standard of living. 

@Skye Penland I should add that I am a traveling nurse with with a weird W2 setup... so that also made things crazy.