These are all unfortunately competing interests that you may need to weigh the pros and cons for as you go forward, including the costs to set up any asset protection or estate planning for your businesses and personal assets.Note: This information is for educational and informational purposes only and does not constitute legal, tax, financial, or investment advice.

Is it for “asset protection” or “anonymity”?

These may affect the asset's depreciation schedule but could also qualify for bonus depreciation themselves.Once your 1099 income moves into an S-Corp or LLC, that structure could also affect how you flow losses, so work closely with your CPA.Consider running a "what if" scenario with your tax advisor to determine the breakeven on doing the cost seg this year.Check if your cost seg provider includes audit protection or support.

Filing a lawsuit and getting in line to be heard can at least provide landlords some protection, or perhaps motivate a tenant to work out a payment plan if this is feasible.

Would you still recommend setting up an LLC or some other corporate structure for liability protection?

These two loan types are among the few exceptions that permit closing directly in the name of an LLC.Most of my clients initially take title in their own name, then later transfer the property into an LLC or land trust for asset protection or tax benefits.

2. have you noticed higher and regular exterior maintence protection (sealing/weatherproofing/termite/bug protection) or anythign?

Consider forming an LLC for liability protection or an S-Corp for tax efficiency if flipping frequently.This post does not create a CPA-Client relationship.

I realize that direct bookings don’t have the protection or support (should something come up) that these platforms provide. 

Are you concerned about co-mingling of funds for asset protection or for some other reason?