I think the best advice is to find something you are comfortable with today and if it appreciates over time you have a nice added bonus.

I thought it would be beneficial to learn even more, plus gain the ability to tour houses and make offers without a middle-man... if I can make some money on the side helping other buy/sell, that's a bonus too.

  ( if less than 50%, cannot use section 179 expense, but can use a  bonus depreciation) You can either claim a bonus depreciation or a section 179 depreciation.

I'm in a position where I can leave my job and live for a bit on a pretty decent bonus.

You can also consider doing cost seg and bonus depreciation on another deal you buy this year to offset the gains.

If you don't want to buy anything, attend sessions you are interested in plus lunch presentations and take lots of notes.Now, if you decide on getting any of the guru courses, many of them will throw extra bonuses and stuff at the event.

Never count on appreciation but invest in a cash flowing property in an area in the path of progress so that if appreciation happens it's a nice bonus!

If so wouldn’t it be beneficial to get a cost segregation done to take advantage of the 100% bonus depreciation to get a bigger refund and invest in another property?

It will want to know your base wages per year, your overtime per year and any bonuses per year, each category done separately.

Similar thing for self-employed, 1099’s, or bonuses/commissions...you have to show track record over multiple years.