In addition to some clarity on the numbers mentioned by @Tom S. it would also be helpful to know the income and expenses on the property to see if paying more or paying higher interest makes sense.

I sit back way to long and I'm  so ready to start my new chapter in my life.

These changes all stem from a lawsuit sitting at the PA Supreme Court about how funding tied to the school district properties is not fair for depressed areas and violates the PA Constitution's edict on education availability.Articles:https://dornish.net/is-pennsylvania-ready-in-2018-to-end-most-property-tax-for-funding-public-schools/https://dornish.net/is-pennsylvania-ready-to-end-most-property-tax-for-funding-public-schools/

Im in Florida Collier county if anyone would like to sit with me.

Move on to the next option or sit and bemoan the fact that someone won't hand over a pile of cash to someone who doesn't want eat their own proverbial cooking, up to you.  

But that just seems ridiculous, since there are about 100+ apartments sitting on a pretty modest piece of land.

The law of averages says I’ll still be in a better position with the toilets because there’s a butt paying me every month that sits on it !

I think Bob needs a reality check on his situation and should agree to a lower amount depending on how bad it is since I'm sure it's unlistable as-is, only marketable to investors that will tear him apart on price.Just be sure that you don' do all the work for a small return while Bob sits on his full amount of $1.8MM. 

From what I can recall back when I looked into investing in Florida, Florida has weird rules regarding HOAs which differ from COAs.

Granted, I could be so far off and none of this matter because the appraisal just isn't there and I just need to sit on an, albeit cash flowing property, without being able to refi for a while.