Again, not a large amount for most people, but I'm trying to squeeze out every penny I can to maximize both my return and the size of my portfolio. 

Gary, as a very tax-concious investor, (my effective tax rate has been negative since 2002) I always keep in mind the land value  to maximize depreciation.

To me it's the height of insanity to expect that you'll be able to maximize your IRR over time as a remote investor with no one on the ground with expertise who's incentivized to maximize this - and don't tell me that's your PM, PMs (perhaps understandably given the business model) are incentivized only by maximizing revenue, nothing to do with controlling cost.

So now that we feel we need to get them out right away, would you dive right in and do some upgrades to maximize rents or should we do a good cleaning, get it rented for a year and pocket some income before updating?

As @David Thompson said hitting $4K a month may be a stretch but you can surly maximize cash flow by either syndicating or partnering with other like minded investors.  

Im a firm believer in house hacking (if i had a family or needed more space) but if you are single and good with renting a room, I would consider an alternative.I would continue renting the room from your friend (assuming the rent and living situation are a good fit for you), and THEN buy the Multi (duplex, quad) or what ever else you can afford.Renting a room from friends keeps your living expenses WAY down, gives you much more flexibility, allows you to live independently and away from your tenants, and allows you to maximize your investment returns on a your up and coming real estate empire.

To abide or adhere to decided cases.It is a general maxim that when a point has been settled by decision, it forms a precedent which is not afterwards to be departed from.

On the other hand, if your goal is maximizing cash flow, rather than building Net Worth, a free and clear property is going to produce more Net Cash Flow.  

I ran the numbers in regards to the taxes, property management, insurance, vacancies, and repair fund and the property was making 34k/year before a profit maximization plan as 8 of tenants have lived there for more than 6 years.3.

You can design your day to maximize your strengths.