People’s Republic of Asheville is more concerned with STR regulations than people living in boxes on the streets.

There is extra costs, more regulation, and more liability. 

I will say the abatement if you do it right with a good contractor will be pricy since they have to abide by some different regulations on disposing of it. 

Owner occuppied loans regualted in every state .. must have state license and NMLS registration.NON owner occ loans on 1 to 4 units are regulated same way in about 15 statesin the other states they are unregulated.Keep in mind though investor loans do not follow the same rules as owner occ and rates can change charges can change closing dates can be blown through etc

The VA and Fha loans have been able to do it but their strict appraisal guidelines make it tough to buy the often older homes in my market in Virginia Beach / Norfolk Area. 

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?

Pick up the phone or stop by local code enforcement offices to make sure that you have a crystal clear understanding of local laws and regulations.

The property will be strictly for investment purposes, not a primary residence.I’ve been looking into two potential financing options:Hard Money Lenders (HML) – I’m drawn to this option for its speed in closing, but I know the rates can be higher.DSCR Loans – This seems like a great option for long-term rentals, but I’m unsure if it’s the right fit for my auction property since it might need some rehabbing.I’m also considering purchasing through a land trust or an LLC to add a layer of protection and privacy.So, my questions are:What’s the best way to approach financing for auction properties?

Underwriting guidelines are more strict than on residential loans, and buyers who might qualify for a condo loan sometimes cannot qualify for an individual tenancy in common loan.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).