I would greatly appreciate any advice you could offer on how to get started with buying your first property also Are there specific resources or strategies you found most helpful when you were starting out? 

That is Plan B for sure.

I normally look to buy units at a 20-30% discount compared to the area and develop a business plan to create equity via forced apprecation, primarily on commercial properties (5+ unit multifamily).

I have insurance either way, but he said it's still best to split them up, with each having their own LLC.My plan is to create a new LLC for each one:-123 MAIN ST, LLC-123 GREEN ST, LLC...and then use my original LLC as the "Holdings Company", which then owns those 2 LLC's, and any additional properties I acquire.As of now, I have 1 business credit card and 1 business account for *JOHN SMITH PROPERTY INVESTMENT, LLC* -- this makes things easy from a bookkeeping standpoint.

But even though we plan to hold the property the reality/risk of not being able to pull equity or sell easily later on without maybe a land contract is kind of concerning?

@Tom Gimer  heck of a stretch of an argument…regulating commerce which IS specifically mentioned in the constitution as a government function doesn’t fall under any of those categories. 

Depending on your plan, some lease terms might work out better or worse.

This would avoid that $800 fee.As always best to contact a trust attorney and tax advisor for your specific situation.Good Investing...

Hoping to learn more about areas you like, the market specific hurdles you’ve encountered and anything else that you like to share would be super appreciated!

Besides this, rather boring, pastime of writing code, I also happen to be extremely passionate about real estate, more specifically multifamily and I decided to launch a new project to develop an MVP of software solution that is tailored to the needs of property managers.