@Bruce Runn @Evan KraljicThank you both for the replies, and thank you Bruce for clarifying the status of the ADU occupancy ordinance.

@Ross Denman   it always kills me when sellers offer to sell for less than market value.. the reality is what your selling it for IS MARKET value if it was worth more you would sell it for more .. that's the American way and simple capitalistic logic.Sounds like your moving into TK  status.. wish you the best with it... there are some new players In Indy...

Make sure you understand what exactly the scope of the search is, if they check for just liens & judgement or do they also check the tax status, federal tax lien search etc.. 

You basically cannot 1031 a property if you own it less than a year, unless you rented it out and then you need an exception to accept 1031 before 1 year.After 1 year, regardless of the status, you can do 1031.I would suggest you learn about credit, lending for flipping, flipping itself...Lenders don't look at Business credit, they look at your personal credit. if you have low credit, the recommendation is to increase it but not mandatory.

Or not worth it due to purchase price/1031/not being a real estate professional status/cost of the seg study?

@Alan Williams I think the question is going to come down to the related party status between the 401K and the LLC. 

If I were you, I'd contact the trustee at 7 days after the sale to find out the status of your Deed.Also, make sure you follow the proper procedure with the tenants.

In these arrangements you have yourself as a direct seller, then you own XYZ which is the same as you since you stand behind that door, you benefit, then you have marital interests in those sold by your wife as well as her entities.

Again, I can't see the documents so don't know what you're dealing with here, but tax exempt entities are not a very straightforward or intuitive area to deal with, and if you structure things improperly, you could risk blowing the tax exempt status which could have major repercussions.

By looking at the numbers, I am also assuming that they want to improve the reserves of Fannie Mae and Freddie Mac so they can be in position to one day be independent of the Federal Government and end their Sponsored entity status.