Since interest rates are now higher than the mortgage on your current home, you'll want to calculate that monthly difference.SIMPLIFIED Example: current house mortgage interest rate is 3%, balance $250k.

Maintenance and potential repairs will also require a long-term financial plan and setting aside a contingency fund for such expenses.The steady cash flow, appreciation over time, and tax benefits can make a meaningful difference to your wealth in the long term, especially with the principal paydown on the mortgage.However, if managing the property from a distance feels too burdensome, or if you’d prefer the certainty and flexibility that comes with having less debt (especially given the high mortgage rates), selling and using the $100,000 in equity to reduce your loan for your next home may be the smarter move.

There are so many variables and some of the biggest misunderstandings come from regional variances on how these variables are handled (mortgages & financing especially).I had thought progressing towards multifamily and then commercial was the obvious path to follow, but one conversation changed it all.

Is it high appreciation area with a low rate mortgage?

It is so much easier to get a HELOC or second mortgage on a primary residence, and much more difficult and expensive to get one on a rental house. 

Fortunately, if your mortgage is backed by Freddie Mac or Fannie Mae, transferring an investment property into an LLC will not trigger acceleration.

If so, can I do this with a conventional mortgage?

The property was occupied (still is) with 1 tenant that I am now having the exhausting pleasure of evicting. 2yrs later, said tenant continues to try every angle to delay the court granted Marshall’s execution.The “2nd” floor was poorly renovated (bad contractors), new tenant moved in and a year later, another eviction process has started as they lost their job and refuse to move or pay.Stuck with a very large mortgage bill (that I am paying), utilities and making small repairs to keep the property up also noting the casual 311 complaints from both tenants. 

Conventional loans with 5% still require mortgage insurance. 

I have my current mortgage as a 25 year (5 year ARM) at 7.5%.