I'm a managing partner at a company that can assist with this.

If you're not conducting the work yourself, contract with reputable and competent companies.

We have been around the bigger pockets community for over a decade now and have more 5 star reviews on bigger pockets than any company on this website in any industry (>270 5 Star reviews).

Hard to produce cash flow or break even with that much debt, at that rate.House-hackers, however enjoy certain one time (non-scalable) advantages that should be taken advantage of in the early days: - They can assume pre-existing debt like VA and FHA Loans (rather than take it on Subject-To which is dramatically riskier).- They can rent by the room and self-manage to produce day 1 cash flow.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

Office space is gutsy at this time with many companies working remotely, maybe part of your investment was to bet that people will be coming back to work in person.  

Ensuring that you provide all of the applicable information to the cost segregation study company helps them provide the most accurate cost benefit analysis.

Depending on the way their company operates, you filing your property as an investment on your taxes may be considered an issue for them depending on how stringent they are.

My company partners with a local contractor.

In those cases, the title company guided us on the necessary steps to resolve the title issues, and we did whatever was required to close the deal.

In our experience, the #1 mistake landlords make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.