So it looks like you would need around 4-5 years to get to break even by selling those stocks and paying the tax now. 

I could get the same or higher overall ROI by putting my money in an index fund which is 100% passive.Deal #2This seems like a good deal to me at the asking price.

So often rentals don't have taxable income; and once they do it's still not subject to the payroll taxes paid by W2 wages or on self employed income. 

Hi Jeffrey, In Florida, when a property is purchased at a foreclosure auction by a third-party bidder (not the bank), the purchaser is generally responsible for unpaid homeowners association (HOA) assessments that accrued prior to the acquisition of the property according to Florida Statutes.

You can use form 3115 to catch up with any depreciation not previously calculated.If you have a condo, it is possible that there is no land allocation.Furthermore, if there were any assessments made by the Condo Association, you want to factor those in as well.

STR, LTR, rent by the room, wrap? 

Originally posted by @Lynnette E.

The majority of homes are owned by homeowners not investors so they fail to put themselves in the shoes of a homeowner or look at data from the standpoint of being in the minority. 

Comparing just those two things, you would save way more money in the long run by avoiding the annual mortgage interest.

A good real estate accountant can save them thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend that they find a tax accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.I would also recommend that they look for a accountant willing to work with them throughout the year, who can help them strategize and who is responsive when they want to know the consequences of the financial decisions they are making throughout the year.Good luck.