We had a plan to build a large real estate portfolio and then sell it in five years and divide the money.

This tax change could trigger even with offering contacts for those services as it could be construed as contractors.

We've never even had a tenant try to sue us over a security deposit dispute.For the last 10+ years, I have occasionally asked for just one example of an investor that was sued, lost, and the judgment exceeded their insurance coverage.

If it's more complicated eviction.com may be your best bet to use they are pretty cost effective.

Co-living also takes quite a bit of money to create more baths, walls, different electrical hookups, etc.

Best bet would be disclose in your listing & disclose again in your welcome message when they book.

Double your money on your 60% left over. 

I would love to be able to bundle them into 1 loan, but have not found a lender who can loan on a single property under $100k, even when bundled with the other one. 

I would like to put the money into purchasing another investment property.

At a minimum look for a deal that breaks even - although it's always better to cash flow and still have the shot at future appreciation.