I just want to know if this is worth pursuing or is it too much of a gamble. 

I want to own my properties in separate LLC's for asset protection, but operate them through one "business" name that I can use for all accounts/transactions (think: Google Voice, email address, web domain, one credit card, paying all the contractors, property manager, etc.) and that one "business" is an LLC separate from the property LLC's. 

It would be much cheaper to hire a CPA that knows what they are doing.See the IRS web site for additional details https://www.irs.gov/businesses...

Flipping property is a gamble.

Are you not transferring the weight of the loaded swing to the glue that binds the added plywood to the webbing? 

I list on Zillow through a online web portal I belong to.  

I also have this same question, but I'm looking for something not cloud or web based, an actual installable program my logic is that I'll be able to create an Air gap between vital information social security numbers/EIN's  bank information account balances and such to keep it from being "hacked" 

I'll assume you understand what is and is not eligible to invest in an OZ and what the benefits of doing so are, and your question is how to do this yourself for BRRRR properties you buy, rehab, etc...rather than just dropping it in a fund (of which there are many, and that's definitely the easier route, though less 'fun').OzToolKit is the best explanation on the web I've found.

But if your business is new and doesn't have the funds to survive some bad months not likely to have folks take a gamble on you if you don't know them.

Import my bank account infoImport my credit card infoImport mortgage statementsImport insurance stmtImport personal w2Import my completed taxes I seriously doubt you you will find everything on that list… much less question why you would need to import a w2… but with that said, we use Rentec-Direct… it is a full service software… collects your rent, tracks all expenses, balances cash / checkbooks, screens tenants, has a tenant  facing web portal… and it really cheap compared to other paid services.