Any entity operating and/or owning property in Ohio, must be registered in Ohio.Rental Income earned in Ohio, must be reported to Ohio.Based on the rest of your questions, it sounds like you were "sold" a series LLC by a "guru".

So for the extra month I had to stay, I renewed my lease for a year then gave them a copy of my orders telling them I was going to break it in a month. 

In some cases if it’s significantly less in the same building it could also mean that the building is not all 100% fee simple and that the very low priced ones are sold leasehold.

I have sold property there as a realtor and I know their inspections are ridiculous and time-consuming, does this apply to wholesaling as well, any help would be appreciated.

Just two months before I looked at it, two similar but larger properties on the same street sold for $802,000 and $1,322,222.

Here in Plymouth County, MA, homes sold over the last 6 months are selling at an average of a bit over 98% of asking price. 

I've used him most on seller financed deals which he sold me and a refi out of a commercial loan.  

I had done well as an owner trading up my principle residence half a dozen times as markets rose during the 80s and 90s but sold out during the dot com bust in 2002 and have been a Silicon Valley renter paying through the nose since then staying close to my tech job.

I just sold a rental home that I use to live on and I am going to be hit with capital gains...

If you sold a property of $100K and are buying a duplex for $200K then you could live in 50% of the property.The valuations n your scenario seem to work but iI think you've got a different potential problem.