I think our modeling has adapted to market changes over the years, so we've stuck with Excel as we can easily change the parameters to keep it "fresh".

Our industry can easily get a bad rap for taking advantage of people.Hey Matt. 

Unfortunately, this reassessment is unavoidable, so you’ll need to evaluate whether transferring the property is worth the potential tax increase.If a Transfer Is Not Feasible:If the potential property tax increase makes the transfer impractical, an alternative option is for your father-in-law to secure a Home Equity Line of Credit (HELOC) on the property.

I think the first place to start is evaluating quality deals.

With a bit of planning and good operations, one can easily manage 20 to 30 properties without an assistant, with less than a day or two a month.There's lots of automated ways to check on rent, make deposits (my tenants deposit directly into a bank account), receive maintenance requests, have maintenance done, etc., etc.One thing I could argue is to have your tenants ONLY email you, especially for maintenance requests, and that email goes directly to the vendor that you have set up to handle it.

Being a licensed agent in New York gives you a great advantage in finding and evaluating deals.

I agree this approach has some risks, so we'll need to evaluate before going all in on it.

As others have noted above, you could easily get overwhelmed if you try to self-manage.

Look at the pictures to evaluate the quality of the materials and workmanship of the comparable sales and align your ARV accordingly. 

You can easily do this on a spreadsheet and it will take less time to track than it would to find and learn a new software.