Some get burned and some hit the jackpot.

Refinancing so frequently burns a lot of wealth in terms of points and closing costs.

There is plenty of money out there, but private investors want to know you are honorable and most have already been burned before.

I still have about 4 that I need to switch over so I should save a little more once I do.But I look at it as free money that just paid for my vacations going forward......No lottery ticket though if a house burns down like I would have had.

I don't want to rely on that, since I know appraisers in our area have been conservative of late and think this is a good enough deal to burn some more midnight oil on to find other methods of funding.

Private investors can come up with some strange requirements, usually they got burned in the past and won't revisit anything like that property again.

Do this so the bank can't burn someone else and secondly, if such items scare away all the other buyers, the bank may come back to you for re-negotiations.You may want to read this thread regarding negotiations with banks.

Once they started repairing the damage, they found that one of the structural supports was burned on one end, but that meant it had to be completely removed/replaced, and a few other major issues.

That brings me to another concern, though, if I don't roll that money into another house, I will take an unwanted, possibley unecessary, tax hit....

It sounds like you have money burning a hole in your pocket, James :-).The tax consequences noted above don’t change because you currently have enough cash.