I'm okay gambling that the FED will reduce rates in the next 2-3 years and then get cashflow post-refi, but want to at least break even until then. 

I am just not a gambling kind of guy and I like to see success connected to how much work I put into something (physically and even better, mentally)Are we just taught that investing in stocks/401K/Roth Ira and similar investments are the way to go and should be part of everyone's portfolio, but maybe for true real estate investors its not needed ?

Procter and Gamble used the same personality test, I think.

The bad news is that finding something STR eligible is not automatic and in many cases you'd have to apply for a permit after you bought, adding a layer of risk, however, you can call ahead of time and understand if permits are available and the property qualifies, so it's not a big gamble.   

It is a bit of a gamble either way, but we definitely still use PropertyRadar because those lists that hit really well get us good deals.

Is that gamble worth it or did I do the right thing and playing it safe and getting a home warranty?

on the flips side I made a 500k flip fee on a 14 lot development.. but I did put up the 50k EM and I did spend about 75k getting it pre plat approved.. then builder closed once all appeals were exhausted.. but I was also prepared to close if he tried to back door me or go around me.. which is not uncommon when you get into the bigger money players.. at the time I did not even realize wholesaling was a thing or you would call it that.. maybe it was a development wholetail since we did put up 125k of risk money :)on the one I just paid the 125k to someone else we have an offer on the table right now from lennar which is a 1mil profit. but again I put up by the time its done 325k to get there.. the mil we get our 325k back then a check for 1 mil if the stars all align .. we could lose 325k also.. rapid appreciation like this I guess those that call appreciation gambling maybe that's exactly what it is... gun slingers.. take me a long time to make 1 mil in a year owing rentals though  LOL..

If not, then he's gambling with your money on his startup concept.

The domestic economy was front-loaded for supply shortages, with the vast majority of production moving off-shore and implementing a JIT supply system.

Banks aren’t willing to gamble right now.