Then we keep the accounting straight via Quickbooks with each unit a different Class.

I'll message you directly a discount link to try it out. 

Offering discounts for weekday or longer stays could also help improve occupancy.

You will also get hit with a tax bill if you sell on that discounted price.

There might be a big discount if you have all your stuff insured with them.

So the best solution is to buy a house needing extensive renovation for cheap and use that discount to change the layout when you bring it up to living standards. 

Many states have discounted property taxes and lower yearly increases for owner occupied properties.

An analysis of the data also shows that the city north of Austin grew 10.6% year-over-year, making it the fastest-growing city of at least 50,000 people. Kyle, south of Austin, ranked No. 2 with a 9% increase to 62,54...

Quote from @Adam Macias: Wholesaling as it is today will be a thing of the past.It’ll truly be strange to even hear people and gurus trying to make big money off it.The more people try wholesaling but then end up not having an end buyer or cancelling contracts or trying weird things like novations, the more all of real estate will be regulated and cause requirements like licensing to be able to transact more than just your personal resident purchase.Which I don't know why hasn't happened sooner.Here's all the states (in red or yellow) requiring a license to wholesale or at least have started the process:Credit: REITipsterI think licensing and regulation is a beautiful thing that should happen if you plan to be an wholesaler and do more than one deal... which is going to be the case for anyone taking this business seriously.Or even it being regulated to need a real estate agent to do more than one deal outside of buying a personal residence.I've had plenty of failed attempts with agents in pursuit of wholesale deals and I know exactly why, it's not because the agent couldn't find me deals, it's just not practical to think there's opportunity for the numbers a wholesaler needs to make a profit on top of everyone else needing to these days.Because the only sellers who truly can sell at a deep enough discount are usually those who ran out of time and just didn't do something sooner with their situation.I know many coaches and gurus will disagree with me but there’s no regulations on youtube gurus and what they teach either.If we look at the current state of the market in hot cities, the availability of online resources to the average homeowner, how many deals can you possibly believe are available at 70% of ARV?

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here.