I don't see the rents in my market, fulfilling the payments on the HELOC and the Traditional, in order to give me enough cashflow to be positive, let alone make the payments.

@Erin AumanYou've made a lot of self-fulfilling statements here:1.

A "second home" loan has nothing to do with the quantity of loans, but instead with the usage intent - which @Scott Stahr's intent fulfills.  

You fulfilled your obligation that the contract outlined.

Also, with this being a STR, there will be an immense amount of turnover which gets back to needing a much higher management fee and/or maintenance for constant cleanliness and upkeep.I certainly hope that there are plenty of other properties that will help you fulfill your goals without being as detrimental to your finances.

I have a good job all things considered, but it’s just not enough...not fulfilling.

I can't speak for every small bank, but my bank does not re-appraise after repairs are complete, they simply inspect with an internal employee to see that your planned list of improvements was fulfilled. 

@Russell Brazil if we all talk about a recession eventually it’ll become a self-fulfilling prophecy.

Setting aside the unpredictability of the timing of a recession or its effect on the economy and/or the real estate market, every single poster who inquires about "waiting for the next recession" presupposes they are actually going to have the nerve to buck societal trends and dire economic warnings, zig when the entire market zags, and buy properties when the market tanks. 

The excess capital generated by the real estate business is used to passively invest in real estate opportunities.Sure, this model is a lot of work... but to exactly John C's point above, i'm not in a rush to leave behind a career that I enjoy, find fulfilling and pays for more than 100% of our lifestyle ... only to 'retire' before the active real estate business has started generating at least as much as the primary day job does.