Whether you need a CPA with just three rentals depends on the complexity of your situation and your comfort level with DIY tax prep.If things are pretty straightforward, you might be fine with tax software for now.

new construction gets valued at a way higher premium. this is a false statement. new construction will always beat existing Very market dependent.

I choose NOT to accept your future. 

I do it manually (and keep in mind, it also depends on the state and location - VRBO does for some and not for others, Airbnb does for some and not for others) I know many folks happy with Avalara though. 

Now this depends on how much you want to raise, if its $1M yeah that can be done, if you go above $5M you are gonna need to spend money and I would assume someone starting out 10% of that amount to get there.

Is your income considered variable in nature depending on job sites and that you do not work a set amount of hours per week?

If you are looking to pull out equity on your home to start to do some fix&flips(great idea) then it would all depend on how much equity there is in you home and your current income(SSI,retirement etc).

Hi Saul, it depends on what you're looking for - cash flow or appreciation?

@Luke Spencer I am not on the management side but I can tell you it took 2+ years to fill 300 units at one of our facilities and the other just hit 300 units in 12/13 months so it really depends on the demographics, and local housing market trend, the more people moving in and out the higher the demand for storage.I think if you're looking at a saturated market then the upfront cash to turn the warehouse into self storage is not a good idea but then again, maybe those operators are on back roads ( low visibility ) and don't push google ads well.

If you choose to go with this strategy you could complete your exchange and immediately do a cash out refi.