Thanks @ramon. my job wouldnt let me leave earlier under any circumstance.

Some states, like CA are more known for their courts allowing the "piercing of the veil" to go after the individuals, but really, in most states it is difficult in circumstances where the LLC has liability for something that happened as a result of the good faith actions of a members where the entity wasn't just a shell entity, but an actual entity with multiple members acting as a company for the purpose of doing business. 

For  1-4 units FHA  when your short sale was due to loss of job, family death ,divorce or other circumstance you should be able to get a mortgage with 20% down after 1 year  10% down after 2 yrs and 3.5% after 3 years There is also new guidelines on self employment income depending if you have given your self a pay check or you have a salaried first job etchttp://themortgagereports.com/18303/mortgage-self-...

Now that I am an agent I can write my own offers and I find that I have a high acceptance rate so far, in other words I don't bother to wirte an offer if the circumstances are not such that I can reasonably expect that it will be accepted.

In-service withdrawals of salary deferral amounts are usually permitted only under hardship circumstances, whereas in-service withdrawals of employer contributions need not be limited to hardship.Withdrawals cannot be more than the participant’s vested account balance, and for participants who have participated in the plan for less than five years, their in-service withdrawal amounts can be further limited to amounts that have been in the plan for two-years or less.Get a copy of the Current Employer SPDOne way of determining if your current employer will allow you access your retirement funds while still working for them, is to check the summary plan description (SPD) for the existing 403b plan.

However, given your circumstance it might be best to collect the subsidized amount for the next couple months then move for eviction at the earliest time that will yield a move out order once the winter moratorium is lifted.Property Management is not for the faint of heart, I agree with @David Dachtera - it might be time to hire a good PM.

I know that we don't meet the exclusion of capital gains because it's been less than 2 years and we don't meet any of the special circumstances.

Of course understanding that there may be circumstances where a hold period of less than a year does not demonstrate an intent to resell (think of an unsolicited offer to purchase, or a job transfer, or a catastrophic illness, or a sudden decline in the attractiveness of the rental due to a neighborhood change).  

Under what circumstances is he on the hook for additional money or a potential loss of money?

The person who was living in the crows nest (seriously, so gross) who they had to have civilly committed to get out was living in one of the other units with some guy, and I should under no circumstances let her move back into the crows nest, and she will ask.