After expenses and mortgage, I end up with a net cash flow of anywhere b/w $150-$250 which I find rather small, and I wonder if this could even get eaten up by tax filing time.

FED cannot avoid cutting rates they dropped in December and January and a CPI index report crushed everything that was really all hedged data.  

South Carolina, specifically Greenville, is often pretty attractive to us just over the line in North Carolina, but keep in mind that as an investor you'll pay MUCH higher property taxes there. 

For $500 you just avoided a lawsuit and/or lawyers consultation. 

Is it worth waiting until September and hope the market is still as strong or take the hit on capital gain taxes and sell now.Secondly, if we do hold this property would it make more sense to prioritize debt paydown (instead of investing in another property, put our cash towards our mortgage payment and have it paid off within 10 years.

I am looking for best practices both from a legal protection standpoint and from a tax advantage standpoint.

For property owners with out-of-state investments, is it necessary to keep all receipts and invoices for write-offs during tax season, even smaller jobs performed by the PM's handyman?

What is the best way to approach this from a property tax standpoint?

A lot of times when there's a big assessment coming up, owners will sell to avoid it. 

My first two properties are still in my personal name and I actually need to switch that up finally, so thank for the reminder.Nonetheless, you can definitely still open up an LLC, I just try to avoid putting the cart before the horse.