You won't be forced to de-convert unless you have violations...eventually the city will start fining you.Very critical terms are non-conforming (no violations - grandfathered in) vs. illegal (violations)...

My challenge is that I don't know when exactly I will be able to obtain the STR permit from the city, so I don't want to convert guests too prematurely. 

Eventually, after finally admitting he could not obtain a loan, he failed to return my capital, and completely stopped responding just long enough until the banks were unable to reverse any payments.

You can convert the library and the famil room into bedrooms, giving you 7bed/5bath.Mortgage could be around $3,000 per month.

This is a SFH that was converted to four units a long time ago.  

I've found that there are markets that have a balance of decent cashflow and decent appreciation and that's the type of market I eventually decided to invest in.I'm not too familiar with the different markets down there but I'd highly recommend looking into Candor Realty. 

Since you are already familiar with house hacking, I would consider converting your current home into a rent-by-room or whatever it takes to keep it as a long-term rental, then look for another home you can hack.

Sure, I wo't have the same financing options, but I might be able to work with hard lenders, or perhaps eventually set up a LLC and maybe that will open up some other financing avenues. 

I have a PO Box that i used for that purpose and any other business mail but since converting to ACH i am not sure when its the last time I went by the post office.  

This is an example of someone violating law to make more money, and it could eventually come back to bite them.