As you mentioned, you can take losses from stocks, but your capital losses can only exceed your capital gains by $3,000.

Not to mention they have a dozen other agents just like you busting their tail for them. 

Like you mentioned, frequent crashes, problems uploading photos, weird restrictions on what words can't be used, listings removed for no obvious reason. ....and, to me, the navigation/operation is very unintuitive and cumbersome.

Though fee schedules vary by company, generally speaking, you'll pay more up front for checkbook control and less over time, since the full custodial companies will have transaction fees not to mention the red tape of going through the custodian for all transactions. 

Quote from @Mitch Holmes: I would flip as well, as Chris mentioned.

BTW, in your example since you didn't mention having signs up about the sealcoat (the one very pertinent detail), then of course your office would likely be liable to pay for their shoes.

Steadily is my go to, but I see you mentioned them already. 

.: @Jonathan ChanYour other post mentioned about your mom's SIDRA doing lending. 

The person who gave me a demonstration mentioned that by using it, listings were much better ranked on Airbnb (he emphasized that the listing updates every night, which is good for the algorithm).

One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions.