Looking to connect with an experienced tax professional regarding filings for my 2 STR properties (Gatlinburg & Hollywood FL) which were both recently cost segregated.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I'm also in the process of exploring Terra Notes, but may just stick with Notion, Pipedrive, and Excel.I previously worked at a fund and Excel was used to globally track a decent portfolio (about $100m), to include limited depth loan pacing and management.

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.

It’s worth exploring to see if it aligns with your investment strategy and timeline.

These are professionals with additional training and a stricter code of ethics.

However, you can defer taxes under §1033 involuntary conversion if you elect to reinvest the proceeds into a similar rental property within two years (three years if the government condemns the property or threatens to do so, and four years for a principal residence in a federally declared disaster area).To reduce taxable gain, consider:Electing §1033 treatment and reinvesting the full $300K into a new rental property to defer taxes completely.Partial reinvestment, where only the portion not reinvested is taxable.Properly documenting all replacement costs and property details to ensure IRS compliance.Using cost segregation on the new property to accelerate depreciation and offset future taxable income.Since the §1033 election must be made, consult a tax professional to ensure compliance and maximize deferral benefits.This post does not create a CPA-Client relationship.

As I explore the neighborhoods in NW Philly, any suggestions on reputable agents with experience in those areas? 

Absolutely - East Hill is a really popular area for traveling heath care professionals, as well as military on short term TDY orders who are looking for furnished stays.Keys to success for my condo have been keeping the furniture fresh, and not looking like every other listing out there.

After seeing my brother's success with flix and flip in the bay area over the last 4 years, I decided to explore the same in New York.