And our property management company said it is harder to manage because it is by-the-room leasing which requires specialized software and also requires higher deposits due to higher expected damaged and also most of the leases expire at the same time around June/July.Additionally I was told that the you need to provide more amenities and the ones you provide have to be of larger quantity.

Now if you have already sent him your assignment and OTP he knows when your contract will expire.  

I call a month ago as I see the check will expire and had the retirement plan administrator reissue the check (payable the same way)Someone today just mentioned I had 60 days to deposit the check and complete the transaction -- I found the IRS website where it talks about that - but from my interpretation they are very vague - one part of the site makes it seem the 60 day clock is if you are paid the funds directly ( I was not in the case or at least in my interpretation) -- another part of the site makes it seem any eligible rollover is subject to the 60 day clock.Did I screw myself by not depositing the check yet?  

Depending on the state you can't just buy a property and kick them out you generally have to wait till the lease expires.

However, it's clear to me there is an expiration date on this...retail can just suck the soul right out of you, so my expiration date with this is coming.  

This is a wonderful business - go under the radar - forget agents and their listed properties - work on expired listings and FSBO's 

For the $10,000 EMD I negotiated with the seller to put up $1000 when the contract was signed and the rest when the contingency period expired.

If it has or does expire, the bank will order a new value, which could cause a curve ball for you.

Double check but I think mechanics liens expire after 90 days if the lien holder doesn't begin foreclosure

One of the things he tried to get me to do during the lease signing was to extend the 2 year lease by another year, and when that didn't work, put in writing that a lease renewal would be no more than 1% when the 2 year lease expired.