There isn't a right or a wrong to this and you can evolve emotionally as you become more confidant in your decision making.   

They never boom and bust like Florida or California, but they also never correct like more volatile markets either.Using the wrong technique in a particular market cycle could cost you a lot of money in lost profits— or lost equity. 

Your A/C and furnace are improvements to the HVAC building system, and thus the building unit of property.The $5,000 will most likely have to be capitalized, but there are caveats within the DMSH, as well as other options such as the small taxpayer safe harbor (STSH).Encourage you to work with your tax CPA/EA as they'll know your facts, circumstances, and goals.Eamonn, let m know if I am interpreting this wrong. 

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Maybe I bought the wrong windows, maybe I bought the right ones but only by luck.

What do we think I am doing wrong here?

That's the wrong target.

If you buy real estate in a decent area with healthy cash flow (after a realistic and conservative analysis, it is difficult to go too wrong. 

@Micaiah Cormier Nothing wrong with owner financing :) You would just need to use a title company and make sure everything is properly recorded like a real mortgage so you have protection.

Doesn't help me retire early.But don't get me wrong, I'm not going to do it.