HI Adam,

Marking and incorporating are two different things. Most people don't trade mark their name. The risk is that someone starts using your name intentionally or unintentionally causing confusion. Domain names are a particular problem as domain pirates tend to grab any domain that someone has even google searched. So if you choose not to mark then grab whatever domains you feel you actually need and don't worry about the rest as Google search doesn't care too much about the domain name.

I did start the marking process for my brand. I chose a name that I could use in any context and serves as a root. For example xxxxx Holdings, xxxxx Property Management, xxxxx Consulting, etc. It is a loooooonnnnnngggg process in Canada. I started my application in 2018 and I should have approval by the end of February (so roughly 4 years). And it will cost you several thousand dollars to have a trade market agent to do the work for you. In the US it is much quicker. 

As for incorporating, this is a discussion you should really have with a real estate focused accountant first, followed by a lawyer (or ideally together). What you need very much depends on your specific circumstances and your long term goals. A lawyer will look at it primarily from a liability containment perspective. An accountant will look at it from a tax efficiency and separation of concerns perspective. For example, your investments may be passive income while a wholesale business is generally active income. They would have two different tax treatments. Active business is generally taxed much less than passive income which will be important to you especially if you have retained earnings. An accountant will be your best advisor here. It is a very specialized skill.