I was forced to buy my first house because my roommate moved out and I couldn't afford to live alone.

This not only defers the taxes on the two rental properties but then once they live in the primary residence for at least 2 years that home now qualifies for the Section 121 exclusion on the gain.

If you qualify for both (you've lived in the property long enough and it is used for investment when you sell it) then you get to take both.

I am the first in my family to do REI and my goal is to break the tradition of working for a salary for 40+ yrs only to retire on what I hope will be enough to start living freely.

@William Taylor so many options...Use your RE knowledge to: WholesaleFind rental deals to sell to investors locally or here on BPStart leveraging your personal contacts to build your sales businessFind a motivated seller willing to do seller financing:- Move in worst room or basement, rent out all the other rooms for max cashflow- You could even live in the basement and STR the rest of the house

I studied RE development and investment for my MBA, I am the building inspector for the town where I live and I worked as a contractor before switching to only working on my own deals.

I like the tub (it wasn't cheap, about 12 grand) but there's not great service options where I live and not sure if I would get it again since I mostly have to take care of it. 

Looking for various tax strategies to reduce the reality that a large RV or boat is a grossly depreciating assetI would not have a loan, so claiming it as a primary or secondary residence and claiming the mortgage deduction is not applicable.I sold my primary residence and I have several rental properties which I use as I'm fixing them up.What I'm pondering is living aboard and working aboard developing a new product, while traveling.  

One issue I see with this is that I do not have a real estate license so I don't think that would create any issues with STR management, but as for MTR management it seems like there are certain limitations without a license - any feedback on that would be appreciated-Staging properties primarily for FSBO's as I know properties listed by realtors will typically have an in-house staging offering.

I won't be able to make the cottage legal rental without living in the primary home myself.