May the odds ever be in your favor.

I'd like to change to self-managed. 

I do that because people can always change their mind or have something come up even with just a day or two before move in, this way the fee is always a fee until the day the lease starts and I get rent. 

Don't assume that it is.If a liability claim ever arises against you for injury or death on your property - and it DOES happen - your risk management will be intensely scrutinized by a plaintiff attorney and potentially a judge or jury.

The biggest real estate boom I have ever seen in my life.

You can also be hit with special levies or increases in the fees as well as the condo board changing rules regarding rentals.Three years ago when I was looking at a higher end condo vs a single family home, the comparables in terms of rent were a condo for about $240K with monthly fees of $250 (I think) vs a single family home for $270K. 

The concept of wholesaling is very easy to learn.

In 10 years doing 100s and 100s and 100s of sec 8, not one ever asked me, please rent to me even though I do not have a SD, NEVER happens.

It will probably not positively cash flow while you are living in it (unless you make some changes that I will get to in a sec) but it would still be a win because you would be paying down a mortgage rather than renting and I imagine your monthly housing cost might end up lower, AND you will now benefit from appreciation.

Does the change need to be approved prior to filing taxes?