In the grand scheme of things, yes, you should eventually replace the windows so 1) They operate properly. 2) It doesn't turn away potential tenants or cause maintenance hassles when a new one moves in.3) Tenants have proper egress in case of an emergency (like fire).Now, windows are expensive, so you'll have to decide how much you're willing to spend, based on how much income the property is bringing in.

Therefore, if your rental income doesn't keep up with inflation, you must consistently reduce your monthly expenses or return to work to compensate for decreased purchasing power to maintain your living standard.No matter how many properties you eventually own, unless rents outpace inflation, you can not achieve true financial freedom.Back to Your SituationYou stated, “I don't believe that the property will continue to appreciate or see the rent growth it has seen over the past few years.”

I did not go into much detail but I'm trying to give a baseline for wholesalers to look at so they can eventually dive deeper into the subjects.  

If this was a long term tenant of more than 2 years, I might not charge anything knowing this just gives me extra time to prep the place for my eventual move back in.

We looked into several projects and eventually, I concluded that there is no real reason for me to reinvent my business, other than "just because".

Here’s my situation.Montgomery AlabamaPurchased my first property for $107k with the intention to rent it out eventually.

This is not true real estate investing - you're investing in an investment promoter who may eventually invest some of what you send him into real estate but you'll have zero control over the investment once you send off the funds.

Because eventually the market will turn around and you'll lose the equity, which is worth way more than the rate and again, is tax free.

Good morning,     I would not want the tenant or yourself to purchase a machine that will need to be serviced and eventually replaced. 

You've learned a valuable lesson that all kinds of people in all kinds of businesses eventually learn......check your spam folder regularly.