Quote from @Ivan Terrero: It really depends on the country of origen Can you be more specific? 

Alternatively, I could maybe outsource just the liability component and still save a ton on premiums.10k deductibles are not usually an option.

Are there specific questions or criteria I should use when interviewing potential law firms to ensure they won't be as detached and unreliable as my current firm?

Would recommed proceeding carefully and consider the means of the lowest cost (loss) strategy for your specific situation ...

Feel free to reach out at any time and happy to share more specifics. 

If you want to stay in the active real estate game but not wanting to buy right away you could 1031 into specific DSTs that have a 721UpReit OPTIONAL component.

Alternatively, if I left the unit as is, or added a bedroom for a much smaller cost by removing the dining room, I could rent the entire unit out on a short or medium term basis, for at or above the monthly cost, then look for a separate house hack with a bath already installed.

Thanks, Christie, for giving specific, actionable items.

Are there any specific neighborhoods or areas that you recommend focusing on for good deals?

feel free to post some specific deals here for more detailed feedback.