I've interviewed him twice on my podcast (once with @Chris Seveney and once on my current show), and I thoroughly enjoyed those conversationss. 

It might depend on what state the assets are in, and what state the entity structures in.

Trying to get a split level (not a lot of sqft) on the market in the next three weeks and trying to decide on whether to open the wall between the dining and living room for a feel of openness or leave it as I have heard from two interior designers that the open concept is on the way out as we are more at home and liking our separate areas in the home.Pragmatically speaking the opening of the wall will be mostly a time drain with it being a load bearing wall and having to support the ceiling while rebuilding and all the drywalling necessary.

I've had this line in my profile for like 5 years.

Based on your situation, you will likely need to recapture the depreciation when you convert the property from a rental (STR) to your primary residence in 2025. 

Purchase price: $340,000 Cash invested: $110,000 This is my first rental property.

When you go to sell, you're subject to tax on the amount of profit between your adjusted basis and sale price, not your purchase vs sale price.Recapture is not repaying the depreciation.

My project is expected to exit this year and it appears that will happen as expected and in line with projections or maybe a little better.

As far as home office no longer being an IRS "red flag" I guaranty that if you put a home office deduction on a personal return on Turbo Tax it will move their audit risk needle.

Plenty of lenders able and willing to lend on properties owned by LLC's.