Allowing cost segregation to be another growing pain and benefit to getting better at real estate investing without feeling overwhelmed. 

@Jacob HavlovickBigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

This approach will allow you to focus on the financial benefits rather than the day-to-day operational tasks.Additionally, consider how this rental income will contribute to your overall financial picture.

Keep in mind you will probably have a deductable to pay first.

For your $240K new-build townhouse, a cost seg may make sense if the tax savings outweigh the study cost (~$3K–$6K), especially since you plan to hold it for 10+ years and can benefit from immediate bonus depreciation.For the $380K older townhouse, cost seg with look-back depreciation could provide significant one-time deductions for missed depreciation over the past six years.

Figure out market rents, deduct expenses to determine NOI, deduct cashflow you want, plug remainder into mortgage calc at current interest rate, then add lender's required down payment.That is how much you offer!

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your accountant remotely to expand your options.I would also recommend looking for an accountant willing to work with you throughout the year.

"Good about deductions" sounds a lot like "doesn't make enough money to be a homeowner", so he should keep renting from someone else, and you should do what you're going to do with the money and wisdom you earned.Of course I don't know your son, but I think this is too dicey and you are too close to the situation.  

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You should also consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.