You will never make enough profit or rental tax deductions to beat that.  

Two types of deductions: "before" and "after."

I own the property free and clear so the only annual deductions have been maintenance, repairs, taxes, depreciation. 

Here’s why it might be a smart move:Maximize ROI: With leverage, you can control a larger asset value with a smaller initial investment, potentially increasing your returns as the property appreciates.Preserve Liquidity: Keep your cash available for other investments or emergencies while still participating in lucrative real estate opportunities.Tax Benefits: Deductible mortgage interest and expenses can lower your taxable income, enhancing profitability compared to an all-cash purchase.If you have the means to buy with cash initially, you can later refinance to unlock equity for further investments or improvements.

Would it make more sense to live in old side and work on it while living there and still make rent on other side while losing out on being able to claim expenses as tax deductible or live in updated side and loose out on rent for about 4-6month(1300/month) but be able to claim all expenses as tax deductible.

For example, are there more tax deductions for doing a BRRRR? 

A serious, no-nonsense buyer should totally consider this.Interestingly, most of the people who pursue this route with us are extremely analytical types: quants at hedge funds, engineers, accountants, lawyers, etc...Ok so seller is not screwing up his comps.. and the BAC goes to your office were you deduct I suppose your hourly fee then rebate the difference if any to your buyer.. and if for some reason you put more time into it than the BAC  then the client comes out of pocket to buy a home ???

Then at the end of the month/quarter you just have to do the math to deduct their usage from the total and bill it how you want.Best option for me going forward is to simply not look at properties that aren't individually metered already haha

Buying an investment here also gives you a reason to vacation here and use it as a tax deduction. 

Also, account for all the tax benefits of ownership, such as mortgage interest deductions, depreciation, and deductions associated with expenses.