There are monthly mortgage, taxes, HOA dues and insurance expenses each month, however this still generates great cash flow every month.

- the property is based in Garfield Heights - and that my property tax will be much higher.More details: https://brickbear.ai/share/deal/1/583 Define "area not that great"......It's a high C type area.

I will want to continue to continue to defer the taxes but in an UPREIT.

A big sports bet might offer a quick adrenaline rush but real estate provides tangible long-term rewards like equity growth, passive income, and tax benefits.

Not giving tax advise, so check with your CPA, but I sold a rental after it was my primary for over 2 years and as long as it was considered my primary residence "2 of the last 5 years", I did not have to pay capital gains on my property sale up to the IRS limit. 

The faster you can pay the infamous "dumb tax" the faster you can create wealth. 

Sometimes hard to find this happy medium in rate sheets, though.Another consideration would be taxes - points are typically treated as interest, so if your tax obligations are high this year vs being higher in the future, then this could also impact buying down now vs paying a little more in interest in future years. 

Run the numbers on potential rental income and make sure you’re comfortable with the property’s cash flow after covering your mortgage, taxes, insurance, and any maintenance.

From a tax perspective, keeping the properties separate may allow step-up in basis benefits for your spouse upon inheritance, reducing capital gains taxes.

I guess it's just too many factors to consider and it easy to get overwhelmed and cannot get accurate info and estimation when I conduct analysis (ex. property tax rate, insurance, maintenance fee, rent, repair, closing cost, etc.)