The deal was contingent upon 60 day due diligence and a clean Phase 1 environmental assessment.

However I have had to replace some major appliances recently which had put my in the defecate and added to my motivation to sell (Hot water heater, two refrigerates and a washer/dryer).

And as John said, have as many remote/wifi controls like locks, thermostats, garage door openers, sprinkler controllers (I don't have cameras, but many do).

I’ve personally helped investors across the US, and with over 150 flips under our family's belt in San Diego and a growing BRRR portfolio, I’ve seen what works - and what doesn’t.

We have 10 properties in total on our 'resume.'  5 SFRs that were bought, remodeled, and sold.  4 30+ unit buildings with heavy capex (north of 300K) and a completed ground up construction of the exact unit I am trying to get financing on now.  

Keep an eye on the STR regulations, and as you progress, consider diversifying your portfolio with other asset classes like commercial or single-family rentals for added stability.

If you value short-term savings and a lower initial payment, Option 1 works well.

Unless you go out and get clients, which is a job and a tough one, then don't waste your time and money like I did.I've since put it on hold

With many heirs and a 50-year history, you have no idea what skeletons could be hiding in the closets.

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value.