Especially if it's a property that could use a little makeover (new paint, new flooring, furniture, etc).

To have a performing Airbnb, you need to easily invest $30-60k between furniture, designer fees etc. without even considering hot tub or other big amenities.

I spoke to the pest control guy and confirmed through research, and these german cockroaches don't just "get in" (they don't live outdoors in CT), they are brought in through hatchhicking.

Try living spaces or Nebraska furniture mart for something that's quality, and not 3.5K.

He came in one day talking about spending his life's savings on furniture, renting a U-Haul to drive to Texas, and furnishing 12 apartments for arbitrage that he would manage from Nashville. 

You could legitimately hire family members for property management or maintenance, purchase furniture, make renovations to take advantage of bonus depreciation, or even explore whether your wife could qualify for real estate professional status, which could allow you to deduct losses against ordinary income.With this many rentals, working with a CPA who specializes in real estate is really important and they can help you explore these strategies, maximize deductions, and structure your holdings in a way that supports growth while minimizing taxes.

Have a handyman on call also who can help with repairs and even moving furniture etc. 

Have 3 under 3 so can do outdoor activities but nothing wild

But single-family homes can still compete if land value is low or outdoor improvements are high.Bottom line — it’s not “condo vs. home,” it’s after-tax cash flow vs. headaches.

What are your thoughts on outdoor smokers?