These are things I wouldn't attempt myself because it's not my field of expertise. 

However, we do not allow tenants to prune our trees and bushes, as these are foundation plants that require a higher level of expertise than most tenants have.For our multiplexes we assume responsibility for the yard care/snow removal and factor it into the rent.

Currently, I’m a realtor active in Oregon and Washington, and I'm looking to broaden my expertise.

With some sweat equity, donated professional expertise by my father the HVAC tech, and all my weekends the summer of 2023, I plan to pull almost $200k in equity from the house with a mortgage to continue investing and moving my investments further, and should still have about $100k left.

I would leverage their expertise in your first transactions.

My fear or rather biggest concern is that all these hotel lobby workshops will keep asking for more and more and more with every level of expertise and coaching.

If you decide to rollover your funds into a self-directed IRA, some things to look out for would be custodial fees (every custodian has a different fee structure), funding turn-around time, online account access, customer service (HUGE when investment deadlines are coming up), and knowledge and expertise over self-directed investments and IRS rules (this is extremely helpful when you are new to self-directing, you want to make sure you work with a custodian who can help answer these types of questions for you). 

I'm contemplating if that would be worth it for getting the advice/expertise they have. 

Or would you charge for your time and expertise - especially when those people are more than willing to pay a small premium for it.Please be honest in your reply.

Growing pains aside, I look back fondly at that home as it laid foundation for the expertise I possess today.