So we see some really problems with coverage for things like a hot tub servicing (too dirty), extra cleaning, having a pet, extra guests... etc. 

You just can close on your new property until your old property closes.It may take extra earnest money or removal of certain contingencies. 

Even if it is $25/month, that is an extra $600 over 2 years.

I am being told it would cost extra to do "expedited permitting" which is apparently anything faster than 6 weeks.

What's the best way to do this, and how much would you expect to pay for this extra layer of management/oversight? 

(The extra fees may not hold up in court, but you get the idea...) 

This is particularly unfortunate because I was looking into refinancing 2 of my rental properties, which I was then told by the mortgage broker that because of my huge credit loss that I was likely looking at paying an extra .5% in interest on each loan.My 3-month period is now over and technically my forbearance ends on August 1st.

The extra income is nice, but am I at legal risk with zoning?

Remember there are extra costs when purchasing.

And sign a bunch of extra legalese stating that GC is not responsible for anything that occurred as a result of work performed prior to such and such a date.You will probably find someone, but I wouldn't take the first anxious GC that comes along, because an experienced GC will be very leery about getting involved at this point (and they shouldn't need the work anyway)