My name is Aidan Ahern, I'm based out of Stillwater Oklahoma as I'm a student at Oklahoma State University, and I'm looking to break into real estate investing by way of house hacking a small multi-family!

You can pivot, but if you are trying to do due diligence on how flipping, BRRRR, STR, and syndications would work for you, you will likely get stuck in the mud.Don't think that if you spend three months learning about flipping and decide the numbers don't work for you, you lost time.

I'm thinking I maybe just flip it...but will that deter buyers?

For example my W2 job and my LLC are both in Florida but let's say I buy and flip a property in Georgia are those taxes settled at the time of the sale or is that something I would have to do when I file my taxes normally. 

This means you would need to refinance the current house into a conventional loan before you can get another FHA loan.

House is currently registered as two but want to turn it into a three.

Were those for buy and hold or flips?

I came to know an Englishman whose business was the purchase of very old, very decrepit houses on rather large estates.

This is a good idea and should be done during due diligence after you have the property under contract.There are some contractors that just work with investors and efficiently get the work done on fixer-uppers or flips in a timely and cost effective way.They may charge you for the estimate which is credited to any work you have done.A general contractor is not a replacement for a quality home inspector and the home inspector may find additional work that needs to be done so good to have them there on the same day if possible.Both results and estimates are useful in retrading or renegotiating after the due diligence.To your success!

You get most of the benefits from a central AC without the insane talks of installing ductwork in an old house.