(Even if I am comfortable, I will probably come back here to ask when the time comes just to be sure I'm not missing anything glaring.)So you're thinking that the chances of working out a deal to have the seller cover the closing costs is a long shot and that I should just be patient and keep saving until I have some more cash?

This would avoid the recording tax and probably a reassessment as well.However, in general the tax payer needs to be the same on sale and purchase. 

If the answer to the first two are No and the value of your time is over $0.00 then it's probably not worth it.

Had they had better management over the years, and stayed up on maintenance, the fees probably wouldn't need to be so high now. 

If your credit is poor and you have too much debt, it's probably a decent rate.

Probably would have never known about it if it wasn't for the connection we had with the other deal.

Probably.

Sounds like the granite counters question in another thread to me.Actually if the typical tenant expects it, you should probably do it to be competitive.

And, in most cases, you have probability to assist. 

Probably best to get an addendum added to the contract early in the negotiations for this one.