Has anyone ever had a similar issue to this?

I keep a very healthy amount of reserves to avoid using my insurance unless I have a catastrophic issue.

For the office, it is advisable to begin with home office deduction if one meets the requirements of the law.

Consult with a tax advisor or attorney familiar with both partnership law and real estate to ensure compliance and minimize tax liability.Once under a TIC structure, 1031 exchanges for individual members could allow them to reinvest proceeds from the sale of properties into new ones without triggering immediate capital gains taxes.

These books are filled with practical advice to help you avoid these mistakes that start small and snowball into major issues.

Other than cost overruns and unforeseen issues, I think it's just a question of if this is worth it.

Helps with your debt to income, better opportunities at cash flow, and typically requires less down to purchase.In regards to challenges, I usually build in an extra 10-15% to deal with things that I can't see behind the walls, including dry rot, electrical or plumbing issues, etc.

Quote from @Richa Wardhan: Regular lender financing, we have paid off 70% of our mortgage on the primary residence so we were loaned money without any issue. 

We had an umbrella policy and never had an issue.

But the answer for everyone may differ.Here are the personal attributes I see in those able to achieve a higher than market ROI, enough higher to be able to “scale”.1- Knowledge of real estate principles, real estate law and real estate finance2- Minimum 3 -5 years full time, or near full time experience directly related to real estate investing3- Ability to utilize technology for increased efficiency, capacity, and accuracy4- Excellent hired legal counsel and excellent hired marketing help5- Established method(s) of obtaining consistently high QUALITY deal flow6- Ability to manage and choose people who are NOT employees: Attorneys, Appraisers, Mortgage Brokers, Real Estate Brokers, Title Companies, Surveyors, Marketing Specialists, Accountants, Contractors, Consultants, Property Managers7- A VERIFIABLE track record of success8- Ability to identify, analyze, and negotiate a deal that can be “worked” for “enhanced” ROI9- Some type of competitive advantage; for example for me it’s my ability to analyze and identify mortgage loans that are actually less risky than all other lenders believe (on the investing in debt side), and on the real property side it’s my ability to analyze”pull the trigger” with LESS information than other investors need,  combined with the ability to pay cash, or raise significant capital almost instantly as well as being able to obtain loans at the lowest prime customer bank rate with no recourse or personal liability.