I find that most folks who put an action plan together, neglect to dig deep enough to discover and articulate their why which is probably the most important component of all this planning. 

This is a key component of being a seasoned developer, and many times missed by less seasoned folks.~ Scott

But it would seem appropriate that a gross sale of $1 mil with the components of $700K actual sale and $300K gift, would still require a reinvestment of $1 mil since the gift is made of value to avoid taxation to the recipient so the gain should stay with the donor.

Replacing the vinyl will rarely qualify because I am sure it will be greater than 1) Lesser of 2% of your basis in the property or $10k  for a small taxpayer safe harbor. 2)  a $2500 to qualify for a de minimis safe harbor, if replacing would qualify, usually not being a structural component of a building.  

It’s appreciated quite a bit and we are now looking to extract cash for more investment before rate increases make a refi or helo/heloc detrimental to cash flow.

In some cases having a license is actually detrimental but in other cases it can be useful.

It might be ideal if you get a long term tenant that is a real wear and tear specialist, one that squeezes the last useful life out of all the components... then out with the old, in with the new...Best of luck!

Now, one could argue that if you removed the financing component from home purchases, the market value of properties would be markedly lower, and I wouldn't disagree with that.

If your managing your own properties that you have a clear ownership interest in .. no licesne requiredif your managing properties for your clients IE collecting rent.. negoatiating leases etc.. then yes you need a brokers license with a PM component.. and you would have to work for a broker for 2 years then sit for your principal broker exam pass that and the property manager component..does not matter resi or commercial.. reason is your handling lots of money for investors and or negotiating contracts state wants those folks to be licensed and accountable. 

If you determine the cost of each major component and divide by their expected lives and then add them all up, you’re likely going to get much more than $360 a year.