Has anyone been in a situation where they acquired a condo and operated it as an STR when the HOA did not make the exclusion in their CC&Rs, but then faced resistance from the HOA?

We have operated STRs since 1999 and they had been around long before then (STEs have existed for many decades).  

I have an operate account for my cabin that I pay for as a backup.

@Kayla Givens Do you own the houses where you operate the SL homes?

In the spirit of order of operations, might be helpful to break down in this fashion: 1) With your 401(k), do you have pre-tax money and post-tax Roth funds?

Having someone who has owned and operated a similar asset is worth its weight in gold. 

Calvin Lee,You won't really find a 7 cap Dollar General in a strong suburban to urban core location unless limited years remaining on primary lease term and mostly cash deals or very small financing.The brand new Dollar Generals with upgraded construction all around in strong suburban to urban core areas tend to sell for 5.75 to 6.4 caps with new leases in place.The 7 cap new Dollar Generals tend to be in crap areas weak suburban to rural and cheap construction and many times on septic systems instead of county or city sewer.Every once in awhile in a strong location there might be a 7 cap with 10 years left on a high end Dollar General at 3 million in price or up.These have no rental increases in primary lease term so year over year your income dollar becomes worth less and less.

*If your aunt was cooperative, you may have been able to form some formal operating agreement... although I am not sure how that operating agreement would hold up in your state.1.

Yes, you can ultimately own a property with little/nothing out of pocket when you're done - but when you reposition with today's rates even moderately leveraged stabilized assets can be hard to find cashflow with debt service and a realistic operating expense load.

The way I was explained it was your net operating income minus depreciation yields your net income and you pay tax on that.