.- Risk that prices increase substantially over the next 3-5 years, and outpace any of the benefits aboveLeaning towards selling since it’s hard to pass up free money, I’m not sure prices have much further to go from here, and we’re not sure we’d like to move back to the same home that’s been rented for 3-5 years anyway.

Especially when it goes from mis-managed to well-managed or vice versa.If a property is increasing the NOI, the market’s cap rate is fixed and so the property’s value goes up.So in the situation you describe where NOI is effectively zero but could be a lot higher, you have three choices:1.

I have been making a living at real estate since 1994 and I currently feel like there are no moves left on the "chess board" Valuations imo are reaching an extreme and risk is increasing. 

Besides potential improvements that can be made to increase the income, I'm concerned about additional expenses will I'm sure no doubt will arise once I visit the properties/ am provided the actual financial sheets on the properties.

Offer to upgrade the AC in exchange for a sufficient increase in rent to pay for it.

Interested in to see what your opinions are on an idea of mine. I have a sfh home with a detached garage at the rear of the property, the property is a corner lot with an alley behind the garage so there is access fro...

There are too many variations that could make this increase or decrease based on project complexity. 

If you make a mistake, your losses and problems can dramatically increase.

Some is, some isn't - so If you're serious about getting "creative", you really need to come up with a solid biz plan and consult with an attorney who can help you to put yourself in a defendable position with whatever strategy you come up with / engage in. 

My 9 to 5 job is sales and I have grown increasingly frustrated with the prospect that I am making millions of dollars for somebody else when I could be putting the same effort into my own business thus,  have recently decided to go all in with real estate investing.I have a decent understanding of the process but I am stuck in the analysis phase of how to generate leads for a few hundred to a thousand dollars.