And while that is a worthwhile goal, it ignores that fact that, even without cashflow, investing in a vacation rental will likely beat the pants off of your IRA contribution, which oh, by the way, isn't "cash flowing" either.Let's do a comparison:With your IRA, assume you are 45 years old, have $100,000 in it, and are committed to contributing $12,000 per year for the next 15 years.

It seems legislation effecting real estate investors is changing by the minute here in Colorado.

My medical is $528 a month for a family of four (1-year plan, high deductible, $1M coverage per person) Like with most policies you get a discount, if you pay in full.

This is why many people buy real estate within an entity (LLC) and only buy 1 property per LLC or a few based on their value/equity. 

Each individual mountain town also seems to have more strict STR fees than other areas I've looked into.I know you already said you wanted to avoid CO, but just reiterating that it's probably wise to look elsewhere. 

My main focus is really to reduce the number of closings (due to fees) and to pay the family member back for helping cover some previous work.

Some restaurants will let you bring a bottle of wine , but charge you a corkage fee. 

Remember in North Carolina there is a (considerable) diligence fees with any offer you make.

One year ago, a business owner purchased the land next to us and now operates firearms weekly, sometimes 15-20 hours per week of shooting.  

There are some minor exceptions, but pretty much you pay the same day, and in some places like 5 minutes after the sale or you even pay up front before you bid and then get your money back if you don't win.Good luck and best wishes....happy bidding.