I'm not leaving my hvac job until I buy a my first investment, but 5 years is to long of a time frame. by the time I purchase my first place I'll be 10 months or so into having a 1099

Brian, I reckon your "skin in the game" should really be the deposit you've saved (over the last 9+ years) to directly buy property that you want to invest in!

Professional landlord" is not a tax term, so I am not positive about what your CPA meant by that.I mentioned a single-LLC setup but he said that that would leave my houses just as vulnerable since they exist in the same corporate entity. 

Cash offer got us to the front of the line, but would consume 75% of the money we have available for investment right now (still leaving enough for one mortgaged rental property).Question.

My tenant caused damage by leaving carpets with excessive cat urine and vomit all over, burnt holes in it with hot coals in a plastic bucket and pretty much never vacuumed stairs, cleaned shower etc etc.She wanted some TV wires back that she left so she was organizing a painter to come and fill the holes and repaint them.

I recently decided to leave that world, mainly because as most of you know, politics suck.

Option A: Leave rents the same...Option B: Split the rent increase with them...Option C: Or pass the full rent increase along to all of them? 

Clarity is key.You don't want to leave the viewer in the dark.

I am going to talk to the property manager tonight (as well as discuss the shoddy nature of the repair - just a small piece of wood attached that didn't even cover half of the broken window on the door leaving the house exposed, and had been that way for a week and a half when I saw it).

My guess is that the underwriter is going to look for the following:- Does the new property fit with what is going on with your life (meaning family - bigger home, kids leaving- smaller home, etc)?