My investment property strategy involves buying smaller properties that are in good school districts near LIRR stations and/or hospitals.
The one exception to this rule is that we bought a potential retirement condo on a golf course in Arizona. We rent it out and take the deductions. We may or may not use it ourselves later on but for now it is not only paying for itself but generating about 18% per annum.
This has been fruitful for the past two decades or so but changes in how income from such sources will be taxed might make it less attractive as a new venture.
At the very least you should have a fat Roth IRA.
I appreciated your tips. Unfortunately I am a tin-foil hat wearing conspiracy theorist. Because of this I have been avoiding 401k and other types of registered money because I fear that the government will confiscate it and/or change the rules to make me regret doing it in the first place. Something like that happened in Canada years ago such that capital gains wound up being better outside of registered retirement funds than inside, from a tax perspective.