In normal circumstances, if you are a seller $ not in a rush, would you take a cash offer to get the money in 10 days, or would you wait another month and get $20K more?

This property came at a discount due to unfortunate circumstances and deferred maintenance.

Since attending graduate school was not foreseen when you purchased the property, its a good chance that it will be considered an unforeseen circumstance and you will be allowed a partial exclusion.

But there could always be circumstances where a shorter (or longer) hold period was called for.  

Then I call applicants to see what move-in date they are looking for and I'll ask them why they are moving -- sometimes they rule themselves out running their mouth.If the employer or pay looks marginal, sometimes I'll call the employer for a ref and If someone calls me with 'special circumstances'; if I want to consider them, I'll check landlord or personal references too.

I currently own (through various circumstances) my only rental property outright.

Worst case -- we'd capitalize and carve out original basis allocable to the old unit (probably not much) and do a partial asset disposition.The above is general advice, and you should discuss with your tax professional, the one who knows your facts, circumstances, and goals, if you have further questions. 

Do you guys think it’s a safer play to fix and hold in these circumstances right now , or a fix and flip is still good depending on market.

This bill would authorize the owner of an accessory dwelling unit built before January 1, 2020, or built on or after January 1, 2020, under specified circumstances, that receives a notice to correct violations or abate nuisances to request that the enforcement of the violation be delayed for 5 years if correcting the violation is not necessary to protect health and safety, as determined by the enforcement agency, subject to specified requirements....Good luck

But right now due to covid we have a weird circumstance where the market is "doing well" (not really though) and the bond's interest rates are low.