None of this has anything to do with your personal tax return.

It's been 2.5 years since I purchased my first property and now that everything in my personal life has slowed down I'm back on the horse and ready to find my next investment.

Quote from @Havital Miltz: I do not know that if someone is in the hospital you can force them to close, I am not an attorney, but I doubt any court will find in your favor, closings do not always happen exactly on the day that is planned, even if everyone is healthy and well, the wholesaler here is not the reason for the delay so I am not sure what exactly you can sue him/her for, they are also being held up due to the seller not being wellJust give the person some time to get out of the hospital, closing will probably not happen the very next day either, this is really extenuating circumstance. 

Then connect with some hard money lenders (you can find some here on BP as well as some who are typing this right now) and connect with them to understand their product type, what they like to lend on and requirements.Hard money broker is all numbers game of making relationships and helping those that are looking for financing, it starts out slow but if you get with a few good borrowers and lenders it can be pretty decent money to be made.As an example we paid six figures last year to HM brokers. 

A Mortgage Broker,Happy to connect.

The person I would seek advice from is a CPA about this. 

If interested in adding another state / city to the list I am happy to connect - but hopefully this is irrelevant and you are already progressing along well with your purchase!!!!  

I had the initial call with a PadSplit sales person, but I wanted to talk to somebody who's actually doing it to get their perspective and advice.

The energy in person is different for me, and I've made some of my best connections and friends at Chicago meetups.Here is a list of the Chicago event from BP: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of ALL THE CHICAGO MEETUPS that I am happy to share with you. 

The person leaving the trailer there is just to store it there.