Yes, I realize it was the first time, that is why I would cover the cost in an effort to be a good landlord and not discourage my tenants from reporting future issues.

You will also need different levels of staffing to support the various strategies as you are already realizing. 

A smaller paid off portfolio seemed a lot easier to manage so that is the path I was on.. but I've come to the realization if I ever want to accumulate serious wealth I will have to use leverage and scale big. 

I realize there are Regional differences.

A friend of mine in Austin once negotiated a partial buy back option when the seller realized they might want back in if the market soared.. from what I read in Bloomberg, that approach can work well if both sides trust each other.If the tenants’ rent covers your carrying costs, that’s a nice cushion, but you still need to clarify that buy back clause.

If you continue filing taxes jointly the income you realize from your separate property will still need to be explained and redacted, regardless of the type of entity holding the real estate.

Quote from @Keegan Felix: This is all very new to me, but I started listening to the BP podcast about a month ago and realized I have a strong interest in real estate investing.

It was a blessing I just didn't realize it at the time.

Also, there’s much to delve into on of those scenarios, like what type of cashflow or investment do you want, etc. residential, multi-res, small multi-res, commercial, industrial, etc.There seems to be fewer deals around these days and this typically benefits the more experienced and skilled investors but there are always multiple investors that get “tripped-up” in these markets due to them relying on recent “fortunate” market circumstances only to realize the markets cycle and they weren’t prepared or didn’t underwrite properly to account for unforeseen potential.There are more considerations, but this is a start.

I always make sure to help the team but also support them while giving them room to make the position theirs, get them to realize they are part of the company, not just an employee.