Okay, Rand Paul has spoken up, but the rest are just part of the "happy machine" to keep spending our money (while keeping a very large cut, kinda like a mafia loan shark) to give to ourselves to "make us happy".

We're just a small company and I figured I would take a short cut by asking. 

I would just be cautious about taking on such a high cost basis this late in the cycle because when we see the next buyer’s market it will probably cut into your equity.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

I realllllly don’t want to sell because I don’t think it has had enough time to appreciate, but I also don’t want to waste thousands of dollars every year in the likely event that my co-op board will not allow me to keep renting out my place.

Even if you have a "perfect" house, it will not rent if not priced correctly, OR you will be overrented (yes that is a thing) meaning you are leaving money on the table.Marketing is also big - Again depending on the area you want to be on as many relevant channels as possible - Airbnb, VRBO, Booking.com, Zillow, Furnished Finder etc and have a direct booking strategy for repeat guests to cut out the middle men.Best of luck!

Not choosing to do something because you don’t want someone to be paid makes no sense (cutting off ones’s nose to spite one’s face).  

If not they get to go waste someone else’s money.  

I’ve definitely seen this, or rather one part of the bank saying it should be fine and the back office part having a different trip wire for return.Doesn’t mean the tenant didn’t cut it awfully close but I’d let it go as long as it was resolved immediately and the tenant paid any overdraft fee.

Because buying a one-off in those areas and then paying property management is going to cut or kill your profits.If you are doing OOS, you should focus on more turnkey or rent-ready over value add because as a new investor, you are going to lose money on the remote rehab.With a prior bankruptcy, an FHA loan, and 50k from someone else or inheritance, I would think a little more solid about how you want to invest.